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Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones

Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona

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2003
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Authors
Bjelaković, Mira
Pavlović, Vladimir D.
Dabović, Milan
Lorenc, Ljubinka
Article (Published version)
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Abstract
The acid-catalyzed reaction of (Z)- and (E)-B-nor-5,10-seco-ketones 2 and 3 resulted in an intramolecular cyclization to give the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene derivative 8, the 5β-hydroxy-A-nor-1(10)-unsaturated compound 9 and the 5β,10β-dihydroxy A-nor-product 10, from the (Z)-isomer and the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene product 11, from the (E)-isomer. Upon UV-irradiation, the (Z)- and (E)-seco-ketones 2 and 3 underwent a reversible (Z)/(E) and (E)/(Z)-isomerization and in addition to a transannular photocyclization to afford the 10(19)-methylidene derivatives 8 and 11, respectively, while photolysis of the 10(19)-methylidene-B-nor-5,10-seco-ketone 4 gave the oxetane derivative 12.
Kiselo-katalizovana reakcija (Z)- i (E)-B-nor-5,10-seko-ketona 2 i 3 rezultuje u intramolekulskoj ciklizaciji dajući 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski derivat 8, 5β-hidroksi A-nor-1(10)-nezasićeno jedinjenje 9 i 5β,10β-dihidroksi-A-nor-proizvod 10, iz Z-izomera, i 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski proizvod 11, iz E-izomera. (Z)- i (E)-Seko- ketoni 2 i 3 UV-ozračivanjem podležu reverzibilnoj (Z)/(E) odnosno (E)/(Z) izomerizaciji, kao i transanularnoj fotociklizaciji dajući 10(19)-metilidenske derivate 8 odnosno 11, dok se fotolizom 10(19)-metilidenskog-5,10-seko-ketona 4 gradi oksetanski derivat 12.
Keywords:
(Z)- and (E)-B-nor-5,10-secosteroidal ketones / 10(19)-methylidene-B-nor-5,10-secosteroidal ketone / acid-catalyzed reactions / photolytic reactions / mechanistic interpretation
Source:
Journal of the Serbian Chemical Society, 2003, 68, 4-5, 303-312
Publisher:
  • Serbian Chemical Society

DOI: 10.2298/JSC0305303B

ISSN: 0352-5139

WoS: 000183423800009

Scopus: 2-s2.0-0037835592
[ Google Scholar ]
4
4
URI
http://cer.ihtm.bg.ac.rs/handle/123456789/115
Collections
  • Radovi istraživača / Researchers' publications
Institution
IHTM
TY  - JOUR
AU  - Bjelaković, Mira
AU  - Pavlović, Vladimir D.
AU  - Dabović, Milan
AU  - Lorenc, Ljubinka
PY  - 2003
UR  - http://cer.ihtm.bg.ac.rs/handle/123456789/115
AB  - The acid-catalyzed reaction of (Z)- and (E)-B-nor-5,10-seco-ketones 2 and 3 resulted in an intramolecular cyclization to give the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene derivative 8, the 5β-hydroxy-A-nor-1(10)-unsaturated compound 9 and the 5β,10β-dihydroxy A-nor-product 10, from the (Z)-isomer and the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene product 11, from the (E)-isomer. Upon UV-irradiation, the (Z)- and (E)-seco-ketones 2 and 3 underwent a reversible (Z)/(E) and (E)/(Z)-isomerization and in addition to a transannular photocyclization to afford the 10(19)-methylidene derivatives 8 and 11, respectively, while photolysis of the 10(19)-methylidene-B-nor-5,10-seco-ketone 4 gave the oxetane derivative 12.
AB  - Kiselo-katalizovana reakcija (Z)- i (E)-B-nor-5,10-seko-ketona 2 i 3 rezultuje u intramolekulskoj ciklizaciji dajući 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski derivat 8, 5β-hidroksi A-nor-1(10)-nezasićeno jedinjenje 9 i 5β,10β-dihidroksi-A-nor-proizvod 10, iz Z-izomera, i 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski proizvod 11, iz E-izomera. (Z)- i (E)-Seko- ketoni 2 i 3 UV-ozračivanjem podležu reverzibilnoj (Z)/(E) odnosno (E)/(Z) izomerizaciji, kao i transanularnoj fotociklizaciji dajući 10(19)-metilidenske derivate 8 odnosno 11, dok se fotolizom 10(19)-metilidenskog-5,10-seko-ketona 4 gradi oksetanski derivat 12.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones
T1  - Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona
VL  - 68
IS  - 4-5
SP  - 303
EP  - 312
DO  - 10.2298/JSC0305303B
ER  - 
@article{
author = "Bjelaković, Mira and Pavlović, Vladimir D. and Dabović, Milan and Lorenc, Ljubinka",
year = "2003",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/115",
abstract = "The acid-catalyzed reaction of (Z)- and (E)-B-nor-5,10-seco-ketones 2 and 3 resulted in an intramolecular cyclization to give the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene derivative 8, the 5β-hydroxy-A-nor-1(10)-unsaturated compound 9 and the 5β,10β-dihydroxy A-nor-product 10, from the (Z)-isomer and the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene product 11, from the (E)-isomer. Upon UV-irradiation, the (Z)- and (E)-seco-ketones 2 and 3 underwent a reversible (Z)/(E) and (E)/(Z)-isomerization and in addition to a transannular photocyclization to afford the 10(19)-methylidene derivatives 8 and 11, respectively, while photolysis of the 10(19)-methylidene-B-nor-5,10-seco-ketone 4 gave the oxetane derivative 12., Kiselo-katalizovana reakcija (Z)- i (E)-B-nor-5,10-seko-ketona 2 i 3 rezultuje u intramolekulskoj ciklizaciji dajući 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski derivat 8, 5β-hidroksi A-nor-1(10)-nezasićeno jedinjenje 9 i 5β,10β-dihidroksi-A-nor-proizvod 10, iz Z-izomera, i 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski proizvod 11, iz E-izomera. (Z)- i (E)-Seko- ketoni 2 i 3 UV-ozračivanjem podležu reverzibilnoj (Z)/(E) odnosno (E)/(Z) izomerizaciji, kao i transanularnoj fotociklizaciji dajući 10(19)-metilidenske derivate 8 odnosno 11, dok se fotolizom 10(19)-metilidenskog-5,10-seko-ketona 4 gradi oksetanski derivat 12.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones, Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona",
volume = "68",
number = "4-5",
pages = "303-312",
doi = "10.2298/JSC0305303B"
}
Bjelaković M, Pavlović VD, Dabović M, Lorenc L. Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona. Journal of the Serbian Chemical Society. 2003;68(4-5):303-312
Bjelaković, M., Pavlović, V. D., Dabović, M.,& Lorenc, L. (2003). Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona.
Journal of the Serbian Chemical SocietySerbian Chemical Society., 68(4-5), 303-312.
https://doi.org/10.2298/JSC0305303B
Bjelaković Mira, Pavlović Vladimir D., Dabović Milan, Lorenc Ljubinka, "Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona" 68, no. 4-5 (2003):303-312,
https://doi.org/10.2298/JSC0305303B .

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