Amino-steroids. Part 6. Stereospecific syntheses of eight, isomeric, steroidal vicinal 2,3-amino-alcohols

Abstract

The seven possible 3-amino-2-hydroxy and 2-amino-3-hydroxy isomers of the anti-arrhythmic steroid, 3α-amino-2β-hydroxy-5α-androstan-17-one, were prepared from 5α-androst-2-en-17-one. The intermediate 2α, 3α- and 2β,3β-epoxides and aziridines were cleaved to vicinal trans-diaxial amino- and azido-alcohols, which, in turn yielded the isomers by a series of functional group inversions and transformations.