Neighboring group participation. Part 14. The preparation of the four stereoisomers of 16-hydroxymethyl-5alpha-androstane-3beta,17-diol.
16alpha-Hydroxymethyl-5alpha-androstane-3beta,17beta-diol and 16beta-hydroxymethyl-5alpha-androstane-3beta,17beta-diol, were obtained from reduction of 16-acetoxymethylene-5alpha-androstan-17-one. The corresponding 16alpha,17alpha- and 16beta,17alpha-hydroxymethyl isomers were obtained by neighboring group participation of the 16- and 17-acetates, respectively. The reactions involving carbocation formation also led to ring D rearrangement products.
Tapolcsányi
P
P
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720, Szeged, Hungary.
Wölfling
J
J
Schneider
G
G
D000732:Androstanols / Q000138:chemical synthesis* / Q000737:chemistry; D002845:Chromatography; D008956:Models, Chemical; D013237:Stereoisomerism; D013696:Temperature
C434326:16-hydroxymethyl-5-androstane-3,17-diol; D000732:Androstanols