Serbian Republic Research Fund

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Serbian Republic Research Fund

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Publications

Non-sensitized photooxygenation of some steroidal isoxazolidines

Lorenc, Ljubinka; Juranić, Ivan; Dabović, Milan; Mihailović, Milhailo Lj.

(Pergamon press, 1991)

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Mihailović, Milhailo Lj.
PY  - 1991
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2698
AB  - UV irradiation of the steroidal isoxazolidines 2a, 2b, and 2c in various solvents in the presence of molecular oxygen, results in oxidative cleavage of the epoxyimino bridge to give several products; the N-unsubstituted isoxazolidine 2a afforded the nitro products 3, 4, and 5 and the azoxy compounds 6 and 7, while the N-methyl and N-acetyl derivatives 2b and 2c produced only the nitro compounds 3 and 5 as sole identifiable material. An explanation of the observed photooxygenation processes involving exciplex formation followed by proton transfer from isaxazolidine to molecular oxygen is presented. © 1991.
PB  - Pergamon press
T2  - Tetrahedron
T1  - Non-sensitized photooxygenation of some steroidal isoxazolidines
VL  - 47
IS  - 32
SP  - 6389
EP  - 6398
DO  - 10.1016/S0040-4020(01)86567-4
ER  - 
@article{
author = "Lorenc, Ljubinka and Juranić, Ivan and Dabović, Milan and Mihailović, Milhailo Lj.",
year = "1991",
abstract = "UV irradiation of the steroidal isoxazolidines 2a, 2b, and 2c in various solvents in the presence of molecular oxygen, results in oxidative cleavage of the epoxyimino bridge to give several products; the N-unsubstituted isoxazolidine 2a afforded the nitro products 3, 4, and 5 and the azoxy compounds 6 and 7, while the N-methyl and N-acetyl derivatives 2b and 2c produced only the nitro compounds 3 and 5 as sole identifiable material. An explanation of the observed photooxygenation processes involving exciplex formation followed by proton transfer from isaxazolidine to molecular oxygen is presented. © 1991.",
publisher = "Pergamon press",
journal = "Tetrahedron",
title = "Non-sensitized photooxygenation of some steroidal isoxazolidines",
volume = "47",
number = "32",
pages = "6389-6398",
doi = "10.1016/S0040-4020(01)86567-4"
}
Lorenc, L., Juranić, I., Dabović, M.,& Mihailović, M. Lj.. (1991). Non-sensitized photooxygenation of some steroidal isoxazolidines. in Tetrahedron
Pergamon press., 47(32), 6389-6398.
https://doi.org/10.1016/S0040-4020(01)86567-4
Lorenc L, Juranić I, Dabović M, Mihailović ML. Non-sensitized photooxygenation of some steroidal isoxazolidines. in Tetrahedron. 1991;47(32):6389-6398.
doi:10.1016/S0040-4020(01)86567-4 .
Lorenc, Ljubinka, Juranić, Ivan, Dabović, Milan, Mihailović, Milhailo Lj., "Non-sensitized photooxygenation of some steroidal isoxazolidines" in Tetrahedron, 47, no. 32 (1991):6389-6398,
https://doi.org/10.1016/S0040-4020(01)86567-4 . .
4
5

Sesquiterpene lactones from Inula helenium

Vajs, Vlatka; Jeremić, Dragoslav; Milosavljević, Slobodan; Macura, Slobodan

(Pergamon Press, 1989)

TY  - JOUR
AU  - Vajs, Vlatka
AU  - Jeremić, Dragoslav
AU  - Milosavljević, Slobodan
AU  - Macura, Slobodan
PY  - 1989
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2792
AB  - The isolation of 11(13)-dehydrocriolin [a germacranolide also known as 11(13)-dehydroivaxillin], 2α-hydroxyalantolactone, 4α,5α-epoxy-10α,14-H-inuviscolide (the major component) and carabrone from the aerial parts of Inula helenium is reported. The first two lactones were isolated for the first time from this plant. © 1989.
PB  - Pergamon Press
T2  - Phytochemistry
T1  - Sesquiterpene lactones from Inula helenium
VL  - 28
IS  - 6
SP  - 1763
EP  - 1764
DO  - 10.1016/S0031-9422(00)97842-7
ER  - 
@article{
author = "Vajs, Vlatka and Jeremić, Dragoslav and Milosavljević, Slobodan and Macura, Slobodan",
year = "1989",
abstract = "The isolation of 11(13)-dehydrocriolin [a germacranolide also known as 11(13)-dehydroivaxillin], 2α-hydroxyalantolactone, 4α,5α-epoxy-10α,14-H-inuviscolide (the major component) and carabrone from the aerial parts of Inula helenium is reported. The first two lactones were isolated for the first time from this plant. © 1989.",
publisher = "Pergamon Press",
journal = "Phytochemistry",
title = "Sesquiterpene lactones from Inula helenium",
volume = "28",
number = "6",
pages = "1763-1764",
doi = "10.1016/S0031-9422(00)97842-7"
}
Vajs, V., Jeremić, D., Milosavljević, S.,& Macura, S.. (1989). Sesquiterpene lactones from Inula helenium. in Phytochemistry
Pergamon Press., 28(6), 1763-1764.
https://doi.org/10.1016/S0031-9422(00)97842-7
Vajs V, Jeremić D, Milosavljević S, Macura S. Sesquiterpene lactones from Inula helenium. in Phytochemistry. 1989;28(6):1763-1764.
doi:10.1016/S0031-9422(00)97842-7 .
Vajs, Vlatka, Jeremić, Dragoslav, Milosavljević, Slobodan, Macura, Slobodan, "Sesquiterpene lactones from Inula helenium" in Phytochemistry, 28, no. 6 (1989):1763-1764,
https://doi.org/10.1016/S0031-9422(00)97842-7 . .
12
16

Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate

Mihailović, Milhailo Lj.; Lorenc, Ljubinka; Dabović, Milan; Bjelaković, Mira

(1988)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Lorenc, Ljubinka
AU  - Dabović, Milan
AU  - Bjelaković, Mira
PY  - 1988
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2699
AB  - The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.
T2  - Tetrahedron
T1  - Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate
VL  - 44
IS  - 19
SP  - 6201
EP  - 6206
DO  - 10.1016/S0040-4020(01)89810-0
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Dabović, Milan and Bjelaković, Mira",
year = "1988",
abstract = "The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.",
journal = "Tetrahedron",
title = "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate",
volume = "44",
number = "19",
pages = "6201-6206",
doi = "10.1016/S0040-4020(01)89810-0"
}
Mihailović, M. Lj., Lorenc, L., Dabović, M.,& Bjelaković, M.. (1988). Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron, 44(19), 6201-6206.
https://doi.org/10.1016/S0040-4020(01)89810-0
Mihailović ML, Lorenc L, Dabović M, Bjelaković M. Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron. 1988;44(19):6201-6206.
doi:10.1016/S0040-4020(01)89810-0 .
Mihailović, Milhailo Lj., Lorenc, Ljubinka, Dabović, Milan, Bjelaković, Mira, "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate" in Tetrahedron, 44, no. 19 (1988):6201-6206,
https://doi.org/10.1016/S0040-4020(01)89810-0 . .
5
4

Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia

Vajs, Vlatka; Jeremić, Dragoslav; Milosavljević, Slobodan; Macura, Slobodan

(John Wiley & Sons Ltd., 1987)

TY  - JOUR
AU  - Vajs, Vlatka
AU  - Jeremić, Dragoslav
AU  - Milosavljević, Slobodan
AU  - Macura, Slobodan
PY  - 1987
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2784
AB  - The application of two‐dimensional NOE NMR spectroscopy (NOESY) for the stereochemical assignment of isomeric 14‐acetoxy‐13‐hydroxy‐ and 13‐acetoxy‐14‐hydroxy‐5,6‐caryophyllen‐7‐ones, and their acetylation products, is reported. Copyright © 1987 John Wiley & Sons Ltd.
PB  - John Wiley & Sons Ltd.
T2  - Magnetic Resonance in Chemistry
T1  - Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia
VL  - 25
IS  - 10
SP  - 889
EP  - 891
DO  - 10.1002/mrc.1260251012
ER  - 
@article{
author = "Vajs, Vlatka and Jeremić, Dragoslav and Milosavljević, Slobodan and Macura, Slobodan",
year = "1987",
abstract = "The application of two‐dimensional NOE NMR spectroscopy (NOESY) for the stereochemical assignment of isomeric 14‐acetoxy‐13‐hydroxy‐ and 13‐acetoxy‐14‐hydroxy‐5,6‐caryophyllen‐7‐ones, and their acetylation products, is reported. Copyright © 1987 John Wiley & Sons Ltd.",
publisher = "John Wiley & Sons Ltd.",
journal = "Magnetic Resonance in Chemistry",
title = "Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia",
volume = "25",
number = "10",
pages = "889-891",
doi = "10.1002/mrc.1260251012"
}
Vajs, V., Jeremić, D., Milosavljević, S.,& Macura, S.. (1987). Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia. in Magnetic Resonance in Chemistry
John Wiley & Sons Ltd.., 25(10), 889-891.
https://doi.org/10.1002/mrc.1260251012
Vajs V, Jeremić D, Milosavljević S, Macura S. Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia. in Magnetic Resonance in Chemistry. 1987;25(10):889-891.
doi:10.1002/mrc.1260251012 .
Vajs, Vlatka, Jeremić, Dragoslav, Milosavljević, Slobodan, Macura, Slobodan, "Two‐dimensional NMR spectra of sesquiterpenes. I—NOESY study of caryophyllenes from Inula spiraeifolia" in Magnetic Resonance in Chemistry, 25, no. 10 (1987):889-891,
https://doi.org/10.1002/mrc.1260251012 . .
3
4

A novel pimara-8(9),15-diene from lycopus europaeus

Jeremić, Dragoslav; Macura, Slobodan; Milosavljević, Slobodan; Vajs, Vlatka

(Pergamon Press, 1985)

TY  - JOUR
AU  - Jeremić, Dragoslav
AU  - Macura, Slobodan
AU  - Milosavljević, Slobodan
AU  - Vajs, Vlatka
PY  - 1985
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2786
AB  - Identification of a novel trioxygenated Δ8(9),15_ pimaric acid methyl ester from plant species Lycopus europaeus by means of two-dimensional 1H NMR spectroscopy (COSY and NOESY) is reported. © 1985.
PB  - Pergamon Press
T2  - Tetrahedron
T1  - A novel pimara-8(9),15-diene from lycopus europaeus
VL  - 41
IS  - 2
SP  - 357
EP  - 364
DO  - 10.1016/S0040-4020(01)96427-0
ER  - 
@article{
author = "Jeremić, Dragoslav and Macura, Slobodan and Milosavljević, Slobodan and Vajs, Vlatka",
year = "1985",
abstract = "Identification of a novel trioxygenated Δ8(9),15_ pimaric acid methyl ester from plant species Lycopus europaeus by means of two-dimensional 1H NMR spectroscopy (COSY and NOESY) is reported. © 1985.",
publisher = "Pergamon Press",
journal = "Tetrahedron",
title = "A novel pimara-8(9),15-diene from lycopus europaeus",
volume = "41",
number = "2",
pages = "357-364",
doi = "10.1016/S0040-4020(01)96427-0"
}
Jeremić, D., Macura, S., Milosavljević, S.,& Vajs, V.. (1985). A novel pimara-8(9),15-diene from lycopus europaeus. in Tetrahedron
Pergamon Press., 41(2), 357-364.
https://doi.org/10.1016/S0040-4020(01)96427-0
Jeremić D, Macura S, Milosavljević S, Vajs V. A novel pimara-8(9),15-diene from lycopus europaeus. in Tetrahedron. 1985;41(2):357-364.
doi:10.1016/S0040-4020(01)96427-0 .
Jeremić, Dragoslav, Macura, Slobodan, Milosavljević, Slobodan, Vajs, Vlatka, "A novel pimara-8(9),15-diene from lycopus europaeus" in Tetrahedron, 41, no. 2 (1985):357-364,
https://doi.org/10.1016/S0040-4020(01)96427-0 . .
13
11

Novel trioxygenated caryophyllenes from Inula Spiraefolia

Jeremić, Dragoslav; Milosavljević, Slobodan; Vajs, Vlatka

(Pergamon Press, 1982)

TY  - JOUR
AU  - Jeremić, Dragoslav
AU  - Milosavljević, Slobodan
AU  - Vajs, Vlatka
PY  - 1982
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2787
AB  - The identification of two novel isomeric trioxygenated caryophyllenes from the plant species Inula Spiraefolia is reported. © 1982.
PB  - Pergamon Press
T2  - Tetrahedron Letters
T1  - Novel trioxygenated caryophyllenes from Inula Spiraefolia
VL  - 23
IS  - 9
SP  - 1009
EP  - 1012
DO  - 10.1016/S0040-4039(00)87007-0
ER  - 
@article{
author = "Jeremić, Dragoslav and Milosavljević, Slobodan and Vajs, Vlatka",
year = "1982",
abstract = "The identification of two novel isomeric trioxygenated caryophyllenes from the plant species Inula Spiraefolia is reported. © 1982.",
publisher = "Pergamon Press",
journal = "Tetrahedron Letters",
title = "Novel trioxygenated caryophyllenes from Inula Spiraefolia",
volume = "23",
number = "9",
pages = "1009-1012",
doi = "10.1016/S0040-4039(00)87007-0"
}
Jeremić, D., Milosavljević, S.,& Vajs, V.. (1982). Novel trioxygenated caryophyllenes from Inula Spiraefolia. in Tetrahedron Letters
Pergamon Press., 23(9), 1009-1012.
https://doi.org/10.1016/S0040-4039(00)87007-0
Jeremić D, Milosavljević S, Vajs V. Novel trioxygenated caryophyllenes from Inula Spiraefolia. in Tetrahedron Letters. 1982;23(9):1009-1012.
doi:10.1016/S0040-4039(00)87007-0 .
Jeremić, Dragoslav, Milosavljević, Slobodan, Vajs, Vlatka, "Novel trioxygenated caryophyllenes from Inula Spiraefolia" in Tetrahedron Letters, 23, no. 9 (1982):1009-1012,
https://doi.org/10.1016/S0040-4039(00)87007-0 . .
6
7

Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates

Lorenc, Ljubinka; Gašić, Miroslav J.; Juranić, Ivan; Dabović, Milan; Minailović, M. Lj.

(Royal Society of Chemistry, 1980)

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Minailović, M. Lj.
PY  - 1980
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2709
AB  - Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.
PB  - Royal Society of Chemistry
T2  - Journal of the Chemical Society, Perkin Transactions 2
T1  - Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates
IS  - 9
SP  - 1356
EP  - 1365
UR  - https://hdl.handle.net/21.15107/rcub_cer_2709
ER  - 
@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Juranić, Ivan and Dabović, Milan and Minailović, M. Lj.",
year = "1980",
abstract = "Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.",
publisher = "Royal Society of Chemistry",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
title = "Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates",
number = "9",
pages = "1356-1365",
url = "https://hdl.handle.net/21.15107/rcub_cer_2709"
}
Lorenc, L., Gašić, M. J., Juranić, I., Dabović, M.,& Minailović, M. Lj.. (1980). Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates. in Journal of the Chemical Society, Perkin Transactions 2
Royal Society of Chemistry.(9), 1356-1365.
https://hdl.handle.net/21.15107/rcub_cer_2709
Lorenc L, Gašić MJ, Juranić I, Dabović M, Minailović ML. Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates. in Journal of the Chemical Society, Perkin Transactions 2. 1980;(9):1356-1365.
https://hdl.handle.net/21.15107/rcub_cer_2709 .
Lorenc, Ljubinka, Gašić, Miroslav J., Juranić, Ivan, Dabović, Milan, Minailović, M. Lj., "Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates" in Journal of the Chemical Society, Perkin Transactions 2, no. 9 (1980):1356-1365,
https://hdl.handle.net/21.15107/rcub_cer_2709 .
4

Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates

Lorenc, Ljubinka; Gašić, Miroslav J.; Dabović, Milan; Vuletić, N; Mihailović, Milhailo Lj.

(Pergamon Press, 1979)

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Dabović, Milan
AU  - Vuletić, N
AU  - Mihailović, Milhailo Lj.
PY  - 1979
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2700
AB  - The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.
PB  - Pergamon Press
T2  - Tetrahedron
T2  - Tetrahedron
T1  - Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates
VL  - 35
IS  - 20
SP  - 2445
EP  - 2452
DO  - 10.1016/S0040-4020(01)93762-7
ER  - 
@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Dabović, Milan and Vuletić, N and Mihailović, Milhailo Lj.",
year = "1979",
abstract = "The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.",
publisher = "Pergamon Press",
journal = "Tetrahedron, Tetrahedron",
title = "Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates",
volume = "35",
number = "20",
pages = "2445-2452",
doi = "10.1016/S0040-4020(01)93762-7"
}
Lorenc, L., Gašić, M. J., Dabović, M., Vuletić, N.,& Mihailović, M. Lj.. (1979). Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates. in Tetrahedron
Pergamon Press., 35(20), 2445-2452.
https://doi.org/10.1016/S0040-4020(01)93762-7
Lorenc L, Gašić MJ, Dabović M, Vuletić N, Mihailović ML. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates. in Tetrahedron. 1979;35(20):2445-2452.
doi:10.1016/S0040-4020(01)93762-7 .
Lorenc, Ljubinka, Gašić, Miroslav J., Dabović, Milan, Vuletić, N, Mihailović, Milhailo Lj., "Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates" in Tetrahedron, 35, no. 20 (1979):2445-2452,
https://doi.org/10.1016/S0040-4020(01)93762-7 . .
1
3

New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds

Mihailović, Milhailo Lj.; Foršek, J.; Lorenc, Ljubinka

(Royal Society of Chemistry, 1978)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Foršek, J.
AU  - Lorenc, Ljubinka
PY  - 1978
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2761
AB  - When 7α-acetoxy-3,3 : 17,17-bis(ethylenedioxy)-5,10-epoxy-5β, 10β-oestran-6-one (2), formed by lead tetra-acetate acetoxylation of the parent compound (1), is heated with alkali, it undergoes ring B aromatization to give 3,3: 17,17-bis(ethylenedioxy)-5(10),6,8-oestratriene-6,7-diol (3), without configurational change at C(14); deacetalization of the corresponding diacetate (4), followed by lead tetra-acetate aromatization of ring A in the resulting diketone (5), produces 6,7-diacetoxy-equilenin (6), which is finally converted into its 3-acetate (7).
PB  - Royal Society of Chemistry
T2  - Journal of the Chemical Society, Chemical Communications
T1  - New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds
IS  - 21
SP  - 916
EP  - 918
DO  - 10.1039/C39780000916
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Foršek, J. and Lorenc, Ljubinka",
year = "1978",
abstract = "When 7α-acetoxy-3,3 : 17,17-bis(ethylenedioxy)-5,10-epoxy-5β, 10β-oestran-6-one (2), formed by lead tetra-acetate acetoxylation of the parent compound (1), is heated with alkali, it undergoes ring B aromatization to give 3,3: 17,17-bis(ethylenedioxy)-5(10),6,8-oestratriene-6,7-diol (3), without configurational change at C(14); deacetalization of the corresponding diacetate (4), followed by lead tetra-acetate aromatization of ring A in the resulting diketone (5), produces 6,7-diacetoxy-equilenin (6), which is finally converted into its 3-acetate (7).",
publisher = "Royal Society of Chemistry",
journal = "Journal of the Chemical Society, Chemical Communications",
title = "New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds",
number = "21",
pages = "916-918",
doi = "10.1039/C39780000916"
}
Mihailović, M. Lj., Foršek, J.,& Lorenc, L.. (1978). New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds. in Journal of the Chemical Society, Chemical Communications
Royal Society of Chemistry.(21), 916-918.
https://doi.org/10.1039/C39780000916
Mihailović ML, Foršek J, Lorenc L. New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds. in Journal of the Chemical Society, Chemical Communications. 1978;(21):916-918.
doi:10.1039/C39780000916 .
Mihailović, Milhailo Lj., Foršek, J., Lorenc, Ljubinka, "New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds" in Journal of the Chemical Society, Chemical Communications, no. 21 (1978):916-918,
https://doi.org/10.1039/C39780000916 . .
3
4

The Reduction of Some 1, 2‐Epoxides with Lithium Aluminium Hydride. Preliminary Communication

Mihailović, Milhailo Lj.; Andrejević, Vladimir; Milovanović, Jovan N.; Janković, Jovan

(Wiley - VCH Verlag GmbH & Co, 1976)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Andrejević, Vladimir
AU  - Milovanović, Jovan N.
AU  - Janković, Jovan
PY  - 1976
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4712
AB  - The factors influencing the ease of the lithium aluminium hydride reduction of various 1,2‐epoxycycloalkanes and 1,2‐epoxyalkanes are described and discussed.
PB  - Wiley - VCH Verlag GmbH & Co
T2  - Helvetica Chimica Acta
T1  - The Reduction of Some 1, 2‐Epoxides with Lithium Aluminium Hydride. Preliminary Communication
VL  - 59
IS  - 7
SP  - 2305
EP  - 2307
DO  - 10.1002/hlca.19760590702
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Andrejević, Vladimir and Milovanović, Jovan N. and Janković, Jovan",
year = "1976",
abstract = "The factors influencing the ease of the lithium aluminium hydride reduction of various 1,2‐epoxycycloalkanes and 1,2‐epoxyalkanes are described and discussed.",
publisher = "Wiley - VCH Verlag GmbH & Co",
journal = "Helvetica Chimica Acta",
title = "The Reduction of Some 1, 2‐Epoxides with Lithium Aluminium Hydride. Preliminary Communication",
volume = "59",
number = "7",
pages = "2305-2307",
doi = "10.1002/hlca.19760590702"
}
Mihailović, M. Lj., Andrejević, V., Milovanović, J. N.,& Janković, J.. (1976). The Reduction of Some 1, 2‐Epoxides with Lithium Aluminium Hydride. Preliminary Communication. in Helvetica Chimica Acta
Wiley - VCH Verlag GmbH & Co., 59(7), 2305-2307.
https://doi.org/10.1002/hlca.19760590702
Mihailović ML, Andrejević V, Milovanović JN, Janković J. The Reduction of Some 1, 2‐Epoxides with Lithium Aluminium Hydride. Preliminary Communication. in Helvetica Chimica Acta. 1976;59(7):2305-2307.
doi:10.1002/hlca.19760590702 .
Mihailović, Milhailo Lj., Andrejević, Vladimir, Milovanović, Jovan N., Janković, Jovan, "The Reduction of Some 1, 2‐Epoxides with Lithium Aluminium Hydride. Preliminary Communication" in Helvetica Chimica Acta, 59, no. 7 (1976):2305-2307,
https://doi.org/10.1002/hlca.19760590702 . .
17
9

Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.

Mihailović, Milhailo Lj.; Dabović, Milan; Lorenc, Ljubinka; Gašić, Miroslav J.

(Pergamon Press, 1970)

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Dabović, Milan
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
PY  - 1970
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2701
PB  - Pergamon Press
T2  - Tetrahedron Letters
T1  - Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.
VL  - 11
IS  - 49
SP  - 4245
EP  - 4248
DO  - 10.1016/S0040-4039(00)89455-1
ER  - 
@article{
author = "Mihailović, Milhailo Lj. and Dabović, Milan and Lorenc, Ljubinka and Gašić, Miroslav J.",
year = "1970",
publisher = "Pergamon Press",
journal = "Tetrahedron Letters",
title = "Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.",
volume = "11",
number = "49",
pages = "4245-4248",
doi = "10.1016/S0040-4039(00)89455-1"
}
Mihailović, M. Lj., Dabović, M., Lorenc, L.,& Gašić, M. J.. (1970). Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.. in Tetrahedron Letters
Pergamon Press., 11(49), 4245-4248.
https://doi.org/10.1016/S0040-4039(00)89455-1
Mihailović ML, Dabović M, Lorenc L, Gašić MJ. Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.. in Tetrahedron Letters. 1970;11(49):4245-4248.
doi:10.1016/S0040-4039(00)89455-1 .
Mihailović, Milhailo Lj., Dabović, Milan, Lorenc, Ljubinka, Gašić, Miroslav J., "Transannular solvolysis reactions in seco-steroids containing a ten-membered ring." in Tetrahedron Letters, 11, no. 49 (1970):4245-4248,
https://doi.org/10.1016/S0040-4039(00)89455-1 . .
2
1