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).
Source:
Journal of the Chemical Society, Chemical Communications, 1978, 21, 916-918
TY - JOUR
AU - Mihailović, Mihailo Lj.
AU - Foršek, J.
AU - Lorenc, Ljubinka
PY - 1978
UR - http://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, Mihailo Lj. and Foršek, J. and Lorenc, Ljubinka",
year = "1978",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2761",
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.
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. Journal of the Chemical Society, Chemical Communications. 1978;(21):916-918
Mihailović Mihailo Lj., Foršek J., Lorenc Ljubinka, "New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds" Journal of the Chemical Society, Chemical Communications, no. 21 (1978):916-918,
https://doi.org/10.1039/C39780000916 .
, 