New approach to the aromatization of ring B in 19-norsteroids and to the synthesis of equilenin-type compounds
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1978
Article (Published version)

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).
Source:
Journal of the Chemical Society, Chemical Communications, 1978, 21, 916-918Publisher:
- Royal Society of Chemistry
Projects:
- Serbian Republic Research Fund