New approach to the aromatization of ringBin 19-norsteroids and to the synthesis of equilenin-type compounds
- 1 January 1978
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 21,p. 916-918
- https://doi.org/10.1039/c39780000916
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).This publication has 2 references indexed in Scilit:
- Über Steroide und Sexualhormone 227. Mitteilung. Die Fragmentierung einwertiger Alkohole mit Blei(IV)‐acetatHelvetica Chimica Acta, 1962
- THE CONSTITUENTS OF ISOEQUILIN AJournal of Biological Chemistry, 1953