Structures and Synthesis of 4a-Homo-7,19-dinorsteroids, X-Ray Crystallography and NMR Spectroscopy

Abstract

X-Ray diffraction revealed the absolute configuration of 4aβ-methyl-4a-homo-7,19-dinor- 5α,10α-androstane-3,17-dione. Detailed NMR analysis suggested that the 5α configuration existed in the starting material, 3β-acetoxy-4a-methylidene-4a-homo-7,19-dinor- 5α-androst-9-en-17-one, and related compounds. Thus 5-methyl-5β-estr-9-ene derivatives with a leaving group in position 6β were found to react with nucleophiles to form rearranged 4a-homo-7,19-dinorandrostane derivatives with a 5α configuration.