Steroid hormones. XXII. Total syntheses of (±)-equilenin methyl ether and (±)-oestrone methyl ether

Abstract

Total syntheses of oestrone methyl ether and equilenin methyl ether are described, based on the Robinson intermediate (1). The key steps are a stereo-specific introduction of the 18-methyl group and the reduction of ring B of the equilenane skeleton, rendered possible by the presence of an 11-carbonyl.