The seven possible 3-amino-2-hydroxy and 2-amino-3-hydroxy isomers of the anti-arrhythmic steroid, 3a-amino-2P-hydroxy-5a-androstan-1 -/-one, were prepared from 5a-androst-2-en-17-one. The intermediate 2a,3a-and 2@,3P-epoxides and aziridines were cleaved to vicinal frans-diaxial amino-and azido-alcohols, which in turn yielded the isomers by a series of functional group inversions and transformations.* An alternative route to the aziridine (30) involved reaction of (25) with p-nitrophenylsulphonyloxyurethane and triethylamine, leading t o the N-ethoxycarbonylaziridine (3 1) which was converted into (30) by potassium hydroxide in ethanol.* Photochemical ring-expansions were unsuccessful, and it is of interest that thermolysis led only to the oxazoline (59), none of the alternative 2p,Sp-isomer being isolated.

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Ausgehend von Δ2‐5α‐Androstenon‐(17) werden 2α,3α‐ und 2β,3β‐Epoxide, Aziridine und Oxazoline dargestellt, die unter unterschiedlichen jeweils untereinander zusammenhängenden Reaktionsfolgen stereospezifisch in die isomeren Aminoalkohole (I) übergeführt werden.

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Reaktion der Steroidaziridine (Ia) bzw. (Ib) mit der Thiosäure (II) liefert die Produkte (III) und (IV) + Dibenzoyldisulfid (DDS) bzw. (V) + (VIa) + (VIb) + (DDS).