Synthesis of 19-norsteroids iii. synthesis and birch reduction of d,1-13-phenyl-18-norestradiol-3-methyl ether

Abstract

d,1-13-Phenyl-18-norestradiol 3-methyl ether (Va) was synthesized by use of 2-phenylcyclopentane-1,3-dione in place of 2-methylcyclopentane-1,3-dione in an established estrone synthesis proceeding from 1,2,3,4-tetrahydro-6-methoxy-1-vinyl-1-naphthol. Conversion of d,1-13-pnenyl-18-nor-estradiol 3-methyl ether (Va) to d,1-13-phenyl-18,19-bisnortestosterone (XI) was possible by a selective Birch reduction providing the C-17 alcohol was masked as a tetrahydropyranyl ether. Alternatively d,1-13-phenyl-18,19-bisnortestosterone (XI) could be prepared from a C-13 dihydrophenyl analog by rearomatization.