New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds
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1978
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Royal Society of Chemistry
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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).
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Journal of the Chemical Society, Chemical Communications, 1978, 21, 916-918Publisher:
- Royal Society of Chemistry
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- Serbian Republic Research Fund
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IHTMTY - 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 . .