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

The seven possible 3-amino-2-hydroxy and 2-amino-3-hydroxy isomers of the anti-arrhythmic steroid, 3a-amino-2ß-hydroxy-5a-androstan-17- one, were prepared from 5a-androst-2-en-17-one. The intermediate 2a,3a- and 2ß,3ß-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.