Stefanović, Milutin

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  • Stefanović, Milutin (15)
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Author's Bibliography

Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides

Milovanović, Mirjana; Pićurić-Jovanović, Ksenija; Đermanović, Miodrag; Đermanović, Verica; Stefanović, Milutin

(Belgrade : Serbian Chemical Society, 2000)

TY  - JOUR
AU  - Milovanović, Mirjana
AU  - Pićurić-Jovanović, Ksenija
AU  - Đermanović, Miodrag
AU  - Đermanović, Verica
AU  - Stefanović, Milutin
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3496
AB  - Investigation of the constituents of the aerial parts of domestic plant species Picris echoides afforded the sesquiterpene lactones, i.e., guaianolides jacquilenin (1), 11-epi-jacquilenin(2), achillin(3) and eudesmanolide telekin(4). The chemical indenti- fication of the two monoterpene glucosides (—)-cix-chrysanthenol-§-D-g1ucopyranoside
(5) and its 6’-acetate 6 is also repoted. The guaianolide achillin (3) and the two monoterpene glucosides 5 and 6 were isolated for the first time from this plant species. Isolation was achieved by column chromatography and the structures were established mainly by the interpretation of their physical and spectral data, which were in agreement with those in the literature
AB  - Из надзменог дела домаће биљне врсте Piscris echoides (фамилија Asteraceae), корова познатог под именом Гргуша, изолована су и идентификована четири сесквитерпенска лактона, као и два монотерпенска глукозида. Идентификовани лактони су гвајанолиди јаквиленин (1), 11-epi-јаквиленин (2) ехилин (3) као и еудесманолид телекин (4). Монотерпенски глукозиди ()- cis- кризантенол-b-D-глукопиранозид (5) и његов 6'-ацетат, 6 су такође изоловани из истог екстракта. Гвајанолид ахилин (3) и монотерпенски глукозиди (5,6) су по први пут изоловани из ове биљне врсте, док су преостала три лактона изолована више пута из европске биљне врсте.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides
T1  - Сесквитерпенски лактони и монотерпенски глукозиди  биљне врсте Picris echoides L.
VL  - 65
IS  - 11
SP  - 763
EP  - 767
DO  - 10.2298/JSC0011763M
ER  - 
@article{
author = "Milovanović, Mirjana and Pićurić-Jovanović, Ksenija and Đermanović, Miodrag and Đermanović, Verica and Stefanović, Milutin",
year = "2000",
abstract = "Investigation of the constituents of the aerial parts of domestic plant species Picris echoides afforded the sesquiterpene lactones, i.e., guaianolides jacquilenin (1), 11-epi-jacquilenin(2), achillin(3) and eudesmanolide telekin(4). The chemical indenti- fication of the two monoterpene glucosides (—)-cix-chrysanthenol-§-D-g1ucopyranoside
(5) and its 6’-acetate 6 is also repoted. The guaianolide achillin (3) and the two monoterpene glucosides 5 and 6 were isolated for the first time from this plant species. Isolation was achieved by column chromatography and the structures were established mainly by the interpretation of their physical and spectral data, which were in agreement with those in the literature, Из надзменог дела домаће биљне врсте Piscris echoides (фамилија Asteraceae), корова познатог под именом Гргуша, изолована су и идентификована четири сесквитерпенска лактона, као и два монотерпенска глукозида. Идентификовани лактони су гвајанолиди јаквиленин (1), 11-epi-јаквиленин (2) ехилин (3) као и еудесманолид телекин (4). Монотерпенски глукозиди ()- cis- кризантенол-b-D-глукопиранозид (5) и његов 6'-ацетат, 6 су такође изоловани из истог екстракта. Гвајанолид ахилин (3) и монотерпенски глукозиди (5,6) су по први пут изоловани из ове биљне врсте, док су преостала три лактона изолована више пута из европске биљне врсте.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides, Сесквитерпенски лактони и монотерпенски глукозиди  биљне врсте Picris echoides L.",
volume = "65",
number = "11",
pages = "763-767",
doi = "10.2298/JSC0011763M"
}
Milovanović, M., Pićurić-Jovanović, K., Đermanović, M., Đermanović, V.,& Stefanović, M.. (2000). Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 65(11), 763-767.
https://doi.org/10.2298/JSC0011763M
Milovanović M, Pićurić-Jovanović K, Đermanović M, Đermanović V, Stefanović M. Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides. in Journal of the Serbian Chemical Society. 2000;65(11):763-767.
doi:10.2298/JSC0011763M .
Milovanović, Mirjana, Pićurić-Jovanović, Ksenija, Đermanović, Miodrag, Đermanović, Verica, Stefanović, Milutin, "Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides" in Journal of the Serbian Chemical Society, 65, no. 11 (2000):763-767,
https://doi.org/10.2298/JSC0011763M . .
6
9
9

Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity

Todorović, Nina; Stefanović, Milutin; Tinant, Bernard; Declercq, Jean-Paul; Makler, Michael T; Šolaja, Bogdan

(Elsevier, 1996)

TY  - JOUR
AU  - Todorović, Nina
AU  - Stefanović, Milutin
AU  - Tinant, Bernard
AU  - Declercq, Jean-Paul
AU  - Makler, Michael T
AU  - Šolaja, Bogdan
PY  - 1996
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3995
AB  - Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5e~- and 5~3-cholestan3-ones by acid-catalyzed addition of hydrogen peroxide to the ketone. They were characterized by IR, NMR, and
mass spectroscopy analysis aided by molecular mechanics calculations, and, in the instance of 5~3-cholestane3et,3~5-dihydroperoxide (6), by x-ray analysis. The synthesized compounds were tested in vitro against Plasmodium falciparum Sierra Leone (D6) and Indochina (W2) malaria clones. All compounds" were inactive to
both clones, with the exception of tetraoxane 7a, which exhibited modest activity toward D6 clone with IC5o =
155 nM
PB  - Elsevier
T2  - Steroids
T1  - Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity
VL  - 61
IS  - 12
SP  - 688
EP  - 696
DO  - 10.1016/S0039-128X(96)00203-6
ER  - 
@article{
author = "Todorović, Nina and Stefanović, Milutin and Tinant, Bernard and Declercq, Jean-Paul and Makler, Michael T and Šolaja, Bogdan",
year = "1996",
abstract = "Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5e~- and 5~3-cholestan3-ones by acid-catalyzed addition of hydrogen peroxide to the ketone. They were characterized by IR, NMR, and
mass spectroscopy analysis aided by molecular mechanics calculations, and, in the instance of 5~3-cholestane3et,3~5-dihydroperoxide (6), by x-ray analysis. The synthesized compounds were tested in vitro against Plasmodium falciparum Sierra Leone (D6) and Indochina (W2) malaria clones. All compounds" were inactive to
both clones, with the exception of tetraoxane 7a, which exhibited modest activity toward D6 clone with IC5o =
155 nM",
publisher = "Elsevier",
journal = "Steroids",
title = "Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity",
volume = "61",
number = "12",
pages = "688-696",
doi = "10.1016/S0039-128X(96)00203-6"
}
Todorović, N., Stefanović, M., Tinant, B., Declercq, J., Makler, M. T.,& Šolaja, B.. (1996). Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity. in Steroids
Elsevier., 61(12), 688-696.
https://doi.org/10.1016/S0039-128X(96)00203-6
Todorović N, Stefanović M, Tinant B, Declercq J, Makler MT, Šolaja B. Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity. in Steroids. 1996;61(12):688-696.
doi:10.1016/S0039-128X(96)00203-6 .
Todorović, Nina, Stefanović, Milutin, Tinant, Bernard, Declercq, Jean-Paul, Makler, Michael T, Šolaja, Bogdan, "Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity" in Steroids, 61, no. 12 (1996):688-696,
https://doi.org/10.1016/S0039-128X(96)00203-6 . .
6
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65
67

Sesquiterpene lactones from Achillea crithmifolia

Milosavljević, Slobodan; Macura, Slobodan; Stefanović, Milutin; Aljančić, Ivana; Milinković, Darinka

(American Chemical Society, 1994)

TY  - JOUR
AU  - Milosavljević, Slobodan
AU  - Macura, Slobodan
AU  - Stefanović, Milutin
AU  - Aljančić, Ivana
AU  - Milinković, Darinka
PY  - 1994
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4375
AB  - The isolation of three highly oxygenated guaianolides, desacetyl-1α-4α- dihydroxybishopsolicepolide [1], its 4β-hydroxy epimer 2 (a new compound), and 1β,2β:3β,4β-diepoxy-8α,10α-dihydroxyguai-12(13)-en-12,6α-olide [3], from the aerial parts of Achillea crithmifolia is reported. Because lactone 3 was shown to be identical with rupin A, the initially proposed 1α,2α:3α,4α-diepoxy stereochemistry of rupin A should be revised.
PB  - American Chemical Society
T2  - Journal of Natural Products
T1  - Sesquiterpene lactones from Achillea crithmifolia
VL  - 57
IS  - 1
SP  - 64
EP  - 67
DO  - 10.1021/np50103a008
ER  - 
@article{
author = "Milosavljević, Slobodan and Macura, Slobodan and Stefanović, Milutin and Aljančić, Ivana and Milinković, Darinka",
year = "1994",
abstract = "The isolation of three highly oxygenated guaianolides, desacetyl-1α-4α- dihydroxybishopsolicepolide [1], its 4β-hydroxy epimer 2 (a new compound), and 1β,2β:3β,4β-diepoxy-8α,10α-dihydroxyguai-12(13)-en-12,6α-olide [3], from the aerial parts of Achillea crithmifolia is reported. Because lactone 3 was shown to be identical with rupin A, the initially proposed 1α,2α:3α,4α-diepoxy stereochemistry of rupin A should be revised.",
publisher = "American Chemical Society",
journal = "Journal of Natural Products",
title = "Sesquiterpene lactones from Achillea crithmifolia",
volume = "57",
number = "1",
pages = "64-67",
doi = "10.1021/np50103a008"
}
Milosavljević, S., Macura, S., Stefanović, M., Aljančić, I.,& Milinković, D.. (1994). Sesquiterpene lactones from Achillea crithmifolia. in Journal of Natural Products
American Chemical Society., 57(1), 64-67.
https://doi.org/10.1021/np50103a008
Milosavljević S, Macura S, Stefanović M, Aljančić I, Milinković D. Sesquiterpene lactones from Achillea crithmifolia. in Journal of Natural Products. 1994;57(1):64-67.
doi:10.1021/np50103a008 .
Milosavljević, Slobodan, Macura, Slobodan, Stefanović, Milutin, Aljančić, Ivana, Milinković, Darinka, "Sesquiterpene lactones from Achillea crithmifolia" in Journal of Natural Products, 57, no. 1 (1994):64-67,
https://doi.org/10.1021/np50103a008 . .
12
15

Sesquiterpene lactones from Achillea crithmifolia

Milosavljević, Slobodan; Aljančić, Ivana; Macura, Slobodan; Milinković, Darinka; Stefanović, Milutin

(Elsevier, 1991)

TY  - JOUR
AU  - Milosavljević, Slobodan
AU  - Aljančić, Ivana
AU  - Macura, Slobodan
AU  - Milinković, Darinka
AU  - Stefanović, Milutin
PY  - 1991
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4376
AB  - The isolation of guaianolides rupicolin-A, rupicolin-B, their acetates and a new germacranolide 1β,10α-epoxy-3β,9β-diacetoxy-11α,13-dihydrocostunolide, identified by means of PS DQF COSY and PS NOESY, from Achillea crithmifolia is reported. A flavonoid jaceidin was also isolated from the same extract.
PB  - Elsevier
T2  - Phytochemistry
T1  - Sesquiterpene lactones from Achillea crithmifolia
VL  - 30
IS  - 10
SP  - 3464
EP  - 3466
DO  - 10.1016/0031-9422(91)83232-A
ER  - 
@article{
author = "Milosavljević, Slobodan and Aljančić, Ivana and Macura, Slobodan and Milinković, Darinka and Stefanović, Milutin",
year = "1991",
abstract = "The isolation of guaianolides rupicolin-A, rupicolin-B, their acetates and a new germacranolide 1β,10α-epoxy-3β,9β-diacetoxy-11α,13-dihydrocostunolide, identified by means of PS DQF COSY and PS NOESY, from Achillea crithmifolia is reported. A flavonoid jaceidin was also isolated from the same extract.",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Sesquiterpene lactones from Achillea crithmifolia",
volume = "30",
number = "10",
pages = "3464-3466",
doi = "10.1016/0031-9422(91)83232-A"
}
Milosavljević, S., Aljančić, I., Macura, S., Milinković, D.,& Stefanović, M.. (1991). Sesquiterpene lactones from Achillea crithmifolia. in Phytochemistry
Elsevier., 30(10), 3464-3466.
https://doi.org/10.1016/0031-9422(91)83232-A
Milosavljević S, Aljančić I, Macura S, Milinković D, Stefanović M. Sesquiterpene lactones from Achillea crithmifolia. in Phytochemistry. 1991;30(10):3464-3466.
doi:10.1016/0031-9422(91)83232-A .
Milosavljević, Slobodan, Aljančić, Ivana, Macura, Slobodan, Milinković, Darinka, Stefanović, Milutin, "Sesquiterpene lactones from Achillea crithmifolia" in Phytochemistry, 30, no. 10 (1991):3464-3466,
https://doi.org/10.1016/0031-9422(91)83232-A . .
20
22

Quercetagetin 6,7,3',4'-tetramethyl ether: a new flavonol from Artemisia annua

Đermanović, Miodrag; Jokić, Aleksandar M.; Jokić, Aleksandar M.; Stefanović, Milutin

(Elsevier, 1975)

TY  - JOUR
AU  - Đermanović, Miodrag
AU  - Jokić, Aleksandar M.
AU  - Jokić, Aleksandar M.
AU  - Stefanović, Milutin
PY  - 1975
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4373
AB  - Plant: Artemisia annua L. Source: South of Belgrade. A CHCl, extract of the whole plant yielded after chromatography a new polar flavonol, yellow crystals, mp 171-172 degrees, M+ m/e 374, C19H18O8. characterized by UV/VIS, the pattern of mass fragmentation, NMR. Methylation gave a hexamethyl ether identical in all respects (mmp, TLC, IR, NMR, UV, MS) to the known quercetagetin hexamethyl ether obtained from an authentic source.
PB  - Elsevier
T2  - Phytochemistry
T1  - Quercetagetin 6,7,3',4'-tetramethyl ether: a new flavonol from Artemisia annua
VL  - 14
IS  - 8
SP  - 1873
DO  - 10.1016/0031-9422(75)85317-9
ER  - 
@article{
author = "Đermanović, Miodrag and Jokić, Aleksandar M. and Jokić, Aleksandar M. and Stefanović, Milutin",
year = "1975",
abstract = "Plant: Artemisia annua L. Source: South of Belgrade. A CHCl, extract of the whole plant yielded after chromatography a new polar flavonol, yellow crystals, mp 171-172 degrees, M+ m/e 374, C19H18O8. characterized by UV/VIS, the pattern of mass fragmentation, NMR. Methylation gave a hexamethyl ether identical in all respects (mmp, TLC, IR, NMR, UV, MS) to the known quercetagetin hexamethyl ether obtained from an authentic source.",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Quercetagetin 6,7,3',4'-tetramethyl ether: a new flavonol from Artemisia annua",
volume = "14",
number = "8",
pages = "1873",
doi = "10.1016/0031-9422(75)85317-9"
}
Đermanović, M., Jokić, A. M., Jokić, A. M.,& Stefanović, M.. (1975). Quercetagetin 6,7,3',4'-tetramethyl ether: a new flavonol from Artemisia annua. in Phytochemistry
Elsevier., 14(8), 1873.
https://doi.org/10.1016/0031-9422(75)85317-9
Đermanović M, Jokić AM, Jokić AM, Stefanović M. Quercetagetin 6,7,3',4'-tetramethyl ether: a new flavonol from Artemisia annua. in Phytochemistry. 1975;14(8):1873.
doi:10.1016/0031-9422(75)85317-9 .
Đermanović, Miodrag, Jokić, Aleksandar M., Jokić, Aleksandar M., Stefanović, Milutin, "Quercetagetin 6,7,3',4'-tetramethyl ether: a new flavonol from Artemisia annua" in Phytochemistry, 14, no. 8 (1975):1873,
https://doi.org/10.1016/0031-9422(75)85317-9 . .
14
18

Extractives of Artemisia scoparia

Stefanović, Milutin; Krstić, Ljubomir; Mladenović, Slobodan

(Elsevier, 1973)

TY  - JOUR
AU  - Stefanović, Milutin
AU  - Krstić, Ljubomir
AU  - Mladenović, Slobodan
PY  - 1973
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4714
AB  - Artemisia scoparia collected south of Belgrade was used. Capillin, 1-phenyl-2,4-hexa-diyne-1-ol, vanillin, and scoparone were isolated. All compounds were identified by direct comparison with authentic materials, by m.m.p., co-chromatography (TLC) and IR and NMR analysis.
PB  - Elsevier
T2  - Phytochemistry
T1  - Extractives of Artemisia scoparia
VL  - 12
IS  - 12
SP  - 2996
EP  - 2997
DO  - 10.1016/0031-9422(73)80524-2
ER  - 
@article{
author = "Stefanović, Milutin and Krstić, Ljubomir and Mladenović, Slobodan",
year = "1973",
abstract = "Artemisia scoparia collected south of Belgrade was used. Capillin, 1-phenyl-2,4-hexa-diyne-1-ol, vanillin, and scoparone were isolated. All compounds were identified by direct comparison with authentic materials, by m.m.p., co-chromatography (TLC) and IR and NMR analysis.",
publisher = "Elsevier",
journal = "Phytochemistry",
title = "Extractives of Artemisia scoparia",
volume = "12",
number = "12",
pages = "2996-2997",
doi = "10.1016/0031-9422(73)80524-2"
}
Stefanović, M., Krstić, L.,& Mladenović, S.. (1973). Extractives of Artemisia scoparia. in Phytochemistry
Elsevier., 12(12), 2996-2997.
https://doi.org/10.1016/0031-9422(73)80524-2
Stefanović M, Krstić L, Mladenović S. Extractives of Artemisia scoparia. in Phytochemistry. 1973;12(12):2996-2997.
doi:10.1016/0031-9422(73)80524-2 .
Stefanović, Milutin, Krstić, Ljubomir, Mladenović, Slobodan, "Extractives of Artemisia scoparia" in Phytochemistry, 12, no. 12 (1973):2996-2997,
https://doi.org/10.1016/0031-9422(73)80524-2 . .
13
11

A new type of sesqiterpene lactone isolated from artemisia annua L. arteannuin B

Jeremić, Dragoslav; Jokić, Aleksandar M.; Behbud, A.; Stefanović, Milutin

(Elsevier, 1973)

TY  - JOUR
AU  - Jeremić, Dragoslav
AU  - Jokić, Aleksandar M.
AU  - Behbud, A.
AU  - Stefanović, Milutin
PY  - 1973
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4207
AB  - The structure of a new sesquiterpene lactone, arteannuin B, isolated from Artemisia annua L. is reported.
PB  - Elsevier
T2  - Tetrahedron Letters
T1  - A new type of sesqiterpene lactone isolated from artemisia annua L. arteannuin B
VL  - 14
IS  - 32
SP  - 3039
EP  - 3042
DO  - 10.1016/S0040-4039(01)96314-2
ER  - 
@article{
author = "Jeremić, Dragoslav and Jokić, Aleksandar M. and Behbud, A. and Stefanović, Milutin",
year = "1973",
abstract = "The structure of a new sesquiterpene lactone, arteannuin B, isolated from Artemisia annua L. is reported.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "A new type of sesqiterpene lactone isolated from artemisia annua L. arteannuin B",
volume = "14",
number = "32",
pages = "3039-3042",
doi = "10.1016/S0040-4039(01)96314-2"
}
Jeremić, D., Jokić, A. M., Behbud, A.,& Stefanović, M.. (1973). A new type of sesqiterpene lactone isolated from artemisia annua L. arteannuin B. in Tetrahedron Letters
Elsevier., 14(32), 3039-3042.
https://doi.org/10.1016/S0040-4039(01)96314-2
Jeremić D, Jokić AM, Behbud A, Stefanović M. A new type of sesqiterpene lactone isolated from artemisia annua L. arteannuin B. in Tetrahedron Letters. 1973;14(32):3039-3042.
doi:10.1016/S0040-4039(01)96314-2 .
Jeremić, Dragoslav, Jokić, Aleksandar M., Behbud, A., Stefanović, Milutin, "A new type of sesqiterpene lactone isolated from artemisia annua L. arteannuin B" in Tetrahedron Letters, 14, no. 32 (1973):3039-3042,
https://doi.org/10.1016/S0040-4039(01)96314-2 . .
3
62
70

Acetoxylation of steroidal lactones by means of lead tetraacetate

Stefanović, Milutin; Djarmati, Z; Gašić, Miroslav

(Elsevier, 1970)

TY  - JOUR
AU  - Stefanović, Milutin
AU  - Djarmati, Z
AU  - Gašić, Miroslav
PY  - 1970
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4664
AB  - One of the structural features of many bitter principles ls the presence of a &-lactone ring. Some of these compounds differ from one another by the state of oxidation of the molecule as a whole and also by the state of oxidation of the lactone ring (Le. chaparrin-glauca rubol) (1). However, the correlation of these compound by direct introduction of an oxygen function Into the lactone ring by chemical means represents a great difficulty.
PB  - Elsevier
T2  - Tetrahedron Letters
T1  - Acetoxylation of steroidal lactones by means of lead tetraacetate
VL  - 11
DO  - 10.1016/S0040-4039(01)98337-6
ER  - 
@article{
author = "Stefanović, Milutin and Djarmati, Z and Gašić, Miroslav",
year = "1970",
abstract = "One of the structural features of many bitter principles ls the presence of a &-lactone ring. Some of these compounds differ from one another by the state of oxidation of the molecule as a whole and also by the state of oxidation of the lactone ring (Le. chaparrin-glauca rubol) (1). However, the correlation of these compound by direct introduction of an oxygen function Into the lactone ring by chemical means represents a great difficulty.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "Acetoxylation of steroidal lactones by means of lead tetraacetate",
volume = "11",
doi = "10.1016/S0040-4039(01)98337-6"
}
Stefanović, M., Djarmati, Z.,& Gašić, M.. (1970). Acetoxylation of steroidal lactones by means of lead tetraacetate. in Tetrahedron Letters
Elsevier., 11.
https://doi.org/10.1016/S0040-4039(01)98337-6
Stefanović M, Djarmati Z, Gašić M. Acetoxylation of steroidal lactones by means of lead tetraacetate. in Tetrahedron Letters. 1970;11.
doi:10.1016/S0040-4039(01)98337-6 .
Stefanović, Milutin, Djarmati, Z, Gašić, Miroslav, "Acetoxylation of steroidal lactones by means of lead tetraacetate" in Tetrahedron Letters, 11 (1970),
https://doi.org/10.1016/S0040-4039(01)98337-6 . .
4
5

Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation

Stefanović, Milutin; Mićović, Ivan V.; Jeremić, Dragoslav; Miljković, Dušan

(Elsevier, 1970)

TY  - JOUR
AU  - Stefanović, Milutin
AU  - Mićović, Ivan V.
AU  - Jeremić, Dragoslav
AU  - Miljković, Dušan
PY  - 1970
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4593
AB  - Intramolecular cyclization by catalytic hydrogenation of 3β-acetoxy-16-picolinylidene-5-androsten-17-one (IV) (80° and 50-60 atm of hydrogen pressure over Pd/C as catalyst) gives rise to the formation of two cyclic products, namely, 5′,6′,7′,8′-tetrahydro-2′αH-3′αH-9′αH-3β-acetoxy-androst-5-eno [16.17-b]indolizine (VII) and its 9′βH-isomer (VIII), in a total yield of over 80%, the ratio of the two isomers being 3:1. The cyclized products have structures similar to naturally occuring alkaloid solanidine. A mechanism is proposed for the cyclization.
PB  - Elsevier
T2  - Tetrahedron
T1  - Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation
VL  - 26
IS  - 11
SP  - 2609
EP  - 2617
DO  - 10.1016/S0040-4020(01)92835-2
ER  - 
@article{
author = "Stefanović, Milutin and Mićović, Ivan V. and Jeremić, Dragoslav and Miljković, Dušan",
year = "1970",
abstract = "Intramolecular cyclization by catalytic hydrogenation of 3β-acetoxy-16-picolinylidene-5-androsten-17-one (IV) (80° and 50-60 atm of hydrogen pressure over Pd/C as catalyst) gives rise to the formation of two cyclic products, namely, 5′,6′,7′,8′-tetrahydro-2′αH-3′αH-9′αH-3β-acetoxy-androst-5-eno [16.17-b]indolizine (VII) and its 9′βH-isomer (VIII), in a total yield of over 80%, the ratio of the two isomers being 3:1. The cyclized products have structures similar to naturally occuring alkaloid solanidine. A mechanism is proposed for the cyclization.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation",
volume = "26",
number = "11",
pages = "2609-2617",
doi = "10.1016/S0040-4020(01)92835-2"
}
Stefanović, M., Mićović, I. V., Jeremić, D.,& Miljković, D.. (1970). Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation. in Tetrahedron
Elsevier., 26(11), 2609-2617.
https://doi.org/10.1016/S0040-4020(01)92835-2
Stefanović M, Mićović IV, Jeremić D, Miljković D. Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation. in Tetrahedron. 1970;26(11):2609-2617.
doi:10.1016/S0040-4020(01)92835-2 .
Stefanović, Milutin, Mićović, Ivan V., Jeremić, Dragoslav, Miljković, Dušan, "Intramolecular cyclization of 3β-acetoxy-16-picolinylidene-5-androsten-17-one by catalytic hydrogenation" in Tetrahedron, 26, no. 11 (1970):2609-2617,
https://doi.org/10.1016/S0040-4020(01)92835-2 . .
7
6

The reaction of lead tetra-acetate with some unbranched α,ω-diols

Mićović, Vukić M.; Stojčić, S.; Bralović, M.; Mladenović, Slobodan; Jeremić, Dragoslav; Stefanović, Milutin

(Elsevier, 1969)

TY  - JOUR
AU  - Mićović, Vukić M.
AU  - Stojčić, S.
AU  - Bralović, M.
AU  - Mladenović, Slobodan
AU  - Jeremić, Dragoslav
AU  - Stefanović, Milutin
PY  - 1969
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4586
AB  - Unbranched α,ω-diols are mainly converted by means of lead tetra-acetate in refluxing benzene to the corresponding ethers of di-α-tetrahydrofuryl, di-α-tetrahydropyryl and/or α-tetrahydrofuryl-α′-tetrahydropyryl type. Thus, 1,6-hexanediol affords cis-1,4-dioxaperhydropentalene (Ia) in 15·2% yield; 1,7-heptanediol affords 1,6-dioxaspiro[4.4]nonane (II) in 29·2% yield; 1,8-octanediol cyclizes to 1,6-dioxaspiro[4.5]decane (IIIa) in 39·3% yield; 1,9-nonanediol affords a mixture of di-α-tetrahydrofurylmethane (IV, 33·2%), 2-(α-tetrahydrofuryl)α′-tetrahydropyran (IVa, 3·7%) and 1,7-di-oxaspiro[5.5]undecane (IVb, 3·3%); 1,10-decanediol is oxidized to a mixture of 1,2-di-α-tetrahydrofurylethane (V, 27·2%), and threo- and erythro-α-tetrahydrofuryl-α′-tetrahydropyrylmethanes (Va, 4·3%); and 1,11-undecanediol affords, as main product, 1,3-di-α-tetrahydrofurylpropane (VI) in 40·1% yield, together with small amounts of four other ethers which were not identified.
PB  - Elsevier
T2  - Tetrahedron
T1  - The reaction of lead tetra-acetate with some unbranched α,ω-diols
VL  - 25
IS  - 5
SP  - 985
EP  - 993
DO  - 10.1016/S0040-4020(01)82671-5
ER  - 
@article{
author = "Mićović, Vukić M. and Stojčić, S. and Bralović, M. and Mladenović, Slobodan and Jeremić, Dragoslav and Stefanović, Milutin",
year = "1969",
abstract = "Unbranched α,ω-diols are mainly converted by means of lead tetra-acetate in refluxing benzene to the corresponding ethers of di-α-tetrahydrofuryl, di-α-tetrahydropyryl and/or α-tetrahydrofuryl-α′-tetrahydropyryl type. Thus, 1,6-hexanediol affords cis-1,4-dioxaperhydropentalene (Ia) in 15·2% yield; 1,7-heptanediol affords 1,6-dioxaspiro[4.4]nonane (II) in 29·2% yield; 1,8-octanediol cyclizes to 1,6-dioxaspiro[4.5]decane (IIIa) in 39·3% yield; 1,9-nonanediol affords a mixture of di-α-tetrahydrofurylmethane (IV, 33·2%), 2-(α-tetrahydrofuryl)α′-tetrahydropyran (IVa, 3·7%) and 1,7-di-oxaspiro[5.5]undecane (IVb, 3·3%); 1,10-decanediol is oxidized to a mixture of 1,2-di-α-tetrahydrofurylethane (V, 27·2%), and threo- and erythro-α-tetrahydrofuryl-α′-tetrahydropyrylmethanes (Va, 4·3%); and 1,11-undecanediol affords, as main product, 1,3-di-α-tetrahydrofurylpropane (VI) in 40·1% yield, together with small amounts of four other ethers which were not identified.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "The reaction of lead tetra-acetate with some unbranched α,ω-diols",
volume = "25",
number = "5",
pages = "985-993",
doi = "10.1016/S0040-4020(01)82671-5"
}
Mićović, V. M., Stojčić, S., Bralović, M., Mladenović, S., Jeremić, D.,& Stefanović, M.. (1969). The reaction of lead tetra-acetate with some unbranched α,ω-diols. in Tetrahedron
Elsevier., 25(5), 985-993.
https://doi.org/10.1016/S0040-4020(01)82671-5
Mićović VM, Stojčić S, Bralović M, Mladenović S, Jeremić D, Stefanović M. The reaction of lead tetra-acetate with some unbranched α,ω-diols. in Tetrahedron. 1969;25(5):985-993.
doi:10.1016/S0040-4020(01)82671-5 .
Mićović, Vukić M., Stojčić, S., Bralović, M., Mladenović, Slobodan, Jeremić, Dragoslav, Stefanović, Milutin, "The reaction of lead tetra-acetate with some unbranched α,ω-diols" in Tetrahedron, 25, no. 5 (1969):985-993,
https://doi.org/10.1016/S0040-4020(01)82671-5 . .
6
16
19

Preparation and photolysis of 2-diazo-6-oximino- and 2,6-bisdiazo-4-tert. Butylcyclohexanone

Tasovac, R.; Stefanović, Milutin; Stojiljković, A.

(Elsevier, 1967)

TY  - JOUR
AU  - Tasovac, R.
AU  - Stefanović, Milutin
AU  - Stojiljković, A.
PY  - 1967
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4666
AB  - Reaction mechanism of diazoketone photolysie is assumed 
to involve the formation ofd-keto-carbene intermediates, final products being dependent on the molecular structure and 
reaction medium. Numerous example8 of Wolff-rearrangement (1) 
1,2-hydrogen shift (2) and intermolecular reactions (3) are available.
PB  - Elsevier
T2  - Tetrahedron Letters
T1  - Preparation and photolysis of 2-diazo-6-oximino- and 2,6-bisdiazo-4-tert. Butylcyclohexanone
VL  - 8
IS  - 28
SP  - 2729
EP  - 2732
DO  - 10.1016/S0040-4039(01)89983-4
ER  - 
@article{
author = "Tasovac, R. and Stefanović, Milutin and Stojiljković, A.",
year = "1967",
abstract = "Reaction mechanism of diazoketone photolysie is assumed 
to involve the formation ofd-keto-carbene intermediates, final products being dependent on the molecular structure and 
reaction medium. Numerous example8 of Wolff-rearrangement (1) 
1,2-hydrogen shift (2) and intermolecular reactions (3) are available.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "Preparation and photolysis of 2-diazo-6-oximino- and 2,6-bisdiazo-4-tert. Butylcyclohexanone",
volume = "8",
number = "28",
pages = "2729-2732",
doi = "10.1016/S0040-4039(01)89983-4"
}
Tasovac, R., Stefanović, M.,& Stojiljković, A.. (1967). Preparation and photolysis of 2-diazo-6-oximino- and 2,6-bisdiazo-4-tert. Butylcyclohexanone. in Tetrahedron Letters
Elsevier., 8(28), 2729-2732.
https://doi.org/10.1016/S0040-4039(01)89983-4
Tasovac R, Stefanović M, Stojiljković A. Preparation and photolysis of 2-diazo-6-oximino- and 2,6-bisdiazo-4-tert. Butylcyclohexanone. in Tetrahedron Letters. 1967;8(28):2729-2732.
doi:10.1016/S0040-4039(01)89983-4 .
Tasovac, R., Stefanović, Milutin, Stojiljković, A., "Preparation and photolysis of 2-diazo-6-oximino- and 2,6-bisdiazo-4-tert. Butylcyclohexanone" in Tetrahedron Letters, 8, no. 28 (1967):2729-2732,
https://doi.org/10.1016/S0040-4039(01)89983-4 . .
3
6

An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids

Stefanović, Milutin; Gašić, Miroslav; Hranisavljević, J.; Đermanović, Miodrag

(Elsevier, 1967)

TY  - JOUR
AU  - Stefanović, Milutin
AU  - Gašić, Miroslav
AU  - Hranisavljević, J.
AU  - Đermanović, Miodrag
PY  - 1967
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4662
AB  - Although microbiological methods of introducing oxygen at C-11 of the steroid molecule are effective, it is obvious that purely synthetic way of producing cortisone and its analogs from bile acids or hecogenin have never been abandoned. Thus, we succeeded to obtain 3alpha-L-acetoxy-11,20-diketo-(5-beta)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids in a very improved yield exceeding 13% calculated on starting deoxycholic acid by the following sequence of reactions.
PB  - Elsevier
T2  - Tetrahedron Letters
T1  - An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids
VL  - 8
IS  - 48
SP  - 4799
EP  - 4803
DO  - 10.1016/S0040-4039(01)89606-4
ER  - 
@article{
author = "Stefanović, Milutin and Gašić, Miroslav and Hranisavljević, J. and Đermanović, Miodrag",
year = "1967",
abstract = "Although microbiological methods of introducing oxygen at C-11 of the steroid molecule are effective, it is obvious that purely synthetic way of producing cortisone and its analogs from bile acids or hecogenin have never been abandoned. Thus, we succeeded to obtain 3alpha-L-acetoxy-11,20-diketo-(5-beta)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids in a very improved yield exceeding 13% calculated on starting deoxycholic acid by the following sequence of reactions.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids",
volume = "8",
number = "48",
pages = "4799-4803",
doi = "10.1016/S0040-4039(01)89606-4"
}
Stefanović, M., Gašić, M., Hranisavljević, J.,& Đermanović, M.. (1967). An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids. in Tetrahedron Letters
Elsevier., 8(48), 4799-4803.
https://doi.org/10.1016/S0040-4039(01)89606-4
Stefanović M, Gašić M, Hranisavljević J, Đermanović M. An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids. in Tetrahedron Letters. 1967;8(48):4799-4803.
doi:10.1016/S0040-4039(01)89606-4 .
Stefanović, Milutin, Gašić, Miroslav, Hranisavljević, J., Đermanović, Miodrag, "An improved preparation of 3-α-acetoxy-11,20-diketo-(5β)-pregnane, the key intermediate in the synthesis of 11-oxygenated corticosteroids" in Tetrahedron Letters, 8, no. 48 (1967):4799-4803,
https://doi.org/10.1016/S0040-4039(01)89606-4 . .
3
1
2

Selective borane reductions of progesterone

Stefanović, Milutin; Lajšić, Stevan D.

(Elsevier, 1967)

TY  - JOUR
AU  - Stefanović, Milutin
AU  - Lajšić, Stevan D.
PY  - 1967
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4661
AB  - A number of selective reductions using borane end metal borohydrides has been described. In our studies of hydroboration of steroid conjugated ketones under different conditions and with different solvents we have found that borane reduces in a good yield the carbonyl group in C-3 of progesterone, without affecting the carbonyl in C-20, as well as the Delta4 double bound, thus giving as the main product, 3beta-hydroxy- 20-keto-Delta4-pregnene, which was obtained in a pure state by direct crystallization of the reaction product from methanol.
PB  - Elsevier
T2  - Tetrahedron Letters
T1  - Selective borane reductions of progesterone
VL  - 8
IS  - 19
SP  - 1777
EP  - 1779
DO  - 10.1016/S0040-4039(00)90721-4
ER  - 
@article{
author = "Stefanović, Milutin and Lajšić, Stevan D.",
year = "1967",
abstract = "A number of selective reductions using borane end metal borohydrides has been described. In our studies of hydroboration of steroid conjugated ketones under different conditions and with different solvents we have found that borane reduces in a good yield the carbonyl group in C-3 of progesterone, without affecting the carbonyl in C-20, as well as the Delta4 double bound, thus giving as the main product, 3beta-hydroxy- 20-keto-Delta4-pregnene, which was obtained in a pure state by direct crystallization of the reaction product from methanol.",
publisher = "Elsevier",
journal = "Tetrahedron Letters",
title = "Selective borane reductions of progesterone",
volume = "8",
number = "19",
pages = "1777-1779",
doi = "10.1016/S0040-4039(00)90721-4"
}
Stefanović, M.,& Lajšić, S. D.. (1967). Selective borane reductions of progesterone. in Tetrahedron Letters
Elsevier., 8(19), 1777-1779.
https://doi.org/10.1016/S0040-4039(00)90721-4
Stefanović M, Lajšić SD. Selective borane reductions of progesterone. in Tetrahedron Letters. 1967;8(19):1777-1779.
doi:10.1016/S0040-4039(00)90721-4 .
Stefanović, Milutin, Lajšić, Stevan D., "Selective borane reductions of progesterone" in Tetrahedron Letters, 8, no. 19 (1967):1777-1779,
https://doi.org/10.1016/S0040-4039(00)90721-4 . .
8
13

Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids

Mihailović, Milhailo Lj.; Lorenc, Ljubinka; Gašić, Miroslav J.; Rogić, Milorad; Melera, A.; Stefanović, Milutin

(Elsevier, 1966)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Rogić, Milorad
AU  - Melera, A.
AU  - Stefanović, Milutin
PY  - 1966
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4161
AB  - Assignment of configuration to the 1,10-double bond in the cis-trans isomeric 3β-acetoxy-5,10-seco-1,10-cholesten-5-ones has been achieved by means of NMR spectrometry. Some reactions of these new compounds have been studied and, as expected from conformational analysis, it was found that only the trans-isomer readily undergoes transannular cyclizations
PB  - Elsevier
T2  - Tetrahedron
T1  - Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids
VL  - 22
IS  - 7
SP  - 2345
EP  - 2358
DO  - 10.1016/S0040-4020(01)82154-2
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Gašić, Miroslav J. and Rogić, Milorad and Melera, A. and Stefanović, Milutin",
year = "1966",
abstract = "Assignment of configuration to the 1,10-double bond in the cis-trans isomeric 3β-acetoxy-5,10-seco-1,10-cholesten-5-ones has been achieved by means of NMR spectrometry. Some reactions of these new compounds have been studied and, as expected from conformational analysis, it was found that only the trans-isomer readily undergoes transannular cyclizations",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids",
volume = "22",
number = "7",
pages = "2345-2358",
doi = "10.1016/S0040-4020(01)82154-2"
}
Mihailović, M. Lj., Lorenc, L., Gašić, M. J., Rogić, M., Melera, A.,& Stefanović, M.. (1966). Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids. in Tetrahedron
Elsevier., 22(7), 2345-2358.
https://doi.org/10.1016/S0040-4020(01)82154-2
Mihailović ML, Lorenc L, Gašić MJ, Rogić M, Melera A, Stefanović M. Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids. in Tetrahedron. 1966;22(7):2345-2358.
doi:10.1016/S0040-4020(01)82154-2 .
Mihailović, Milhailo Lj., Lorenc, Ljubinka, Gašić, Miroslav J., Rogić, Milorad, Melera, A., Stefanović, Milutin, "Configuration and reactivity of ten-membered 5,10-seco-compounds obtained by fragmentation of 5-hydroxy-steroids" in Tetrahedron, 22, no. 7 (1966):2345-2358,
https://doi.org/10.1016/S0040-4020(01)82154-2 . .
60
63

Opening of steroid ring a by means of lead tetraacetate

Stefanović, Milutin; Gašić, Miroslav I.; Lorenc, Ljubinka B.; Mihailović, Milhailo Lj.

(Elsevier, 1964)

TY  - JOUR
AU  - Stefanović, Milutin
AU  - Gašić, Miroslav I.
AU  - Lorenc, Ljubinka B.
AU  - Mihailović, Milhailo Lj.
PY  - 1964
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4538
AB  - The lead tetraacetate oxidation of cholestan-1β-ol and cholestan-1α-ol in benzene solution did not afford cyclic ethers but resulted, in major part, in the opening of ring A with formation of 1,10-seco-aldehydes. In addition, cholestane, cholest-1-ene and cholestan-1-one were also obtained.
PB  - Elsevier
T2  - Tetrahedron
T1  - Opening of steroid ring a by means of lead tetraacetate
VL  - 20
IS  - 10
SP  - 2289
EP  - 2294
DO  - 10.1016/S0040-4020(01)97616-1
ER  - 
@article{
author = "Stefanović, Milutin and Gašić, Miroslav I. and Lorenc, Ljubinka B. and Mihailović, Milhailo Lj.",
year = "1964",
abstract = "The lead tetraacetate oxidation of cholestan-1β-ol and cholestan-1α-ol in benzene solution did not afford cyclic ethers but resulted, in major part, in the opening of ring A with formation of 1,10-seco-aldehydes. In addition, cholestane, cholest-1-ene and cholestan-1-one were also obtained.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Opening of steroid ring a by means of lead tetraacetate",
volume = "20",
number = "10",
pages = "2289-2294",
doi = "10.1016/S0040-4020(01)97616-1"
}
Stefanović, M., Gašić, M. I., Lorenc, L. B.,& Mihailović, M. Lj.. (1964). Opening of steroid ring a by means of lead tetraacetate. in Tetrahedron
Elsevier., 20(10), 2289-2294.
https://doi.org/10.1016/S0040-4020(01)97616-1
Stefanović M, Gašić MI, Lorenc LB, Mihailović ML. Opening of steroid ring a by means of lead tetraacetate. in Tetrahedron. 1964;20(10):2289-2294.
doi:10.1016/S0040-4020(01)97616-1 .
Stefanović, Milutin, Gašić, Miroslav I., Lorenc, Ljubinka B., Mihailović, Milhailo Lj., "Opening of steroid ring a by means of lead tetraacetate" in Tetrahedron, 20, no. 10 (1964):2289-2294,
https://doi.org/10.1016/S0040-4020(01)97616-1 . .
14
5