Neighboring group participation. Part 14. The preparation of the four stereoisomers of 16-hydroxymethyl-5α-androstane-3β,17-diol

16α-Hydroxymethyl-5α-androstane-3β,17β-diol and 16β-hydroxymethyl-5α-androstane-3β,17β-diol, were obtained from reduction of 16-acetoxymethylene-5α-androstan-17-one. The corresponding 16α,17α- and 16β,17α-hydroxymethyl isomers were obtained by neighboring group participation of the 16- and 17-acetat...

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Veröffentlicht in:	Steroids 2001, Vol.66 (8), p.623-635
Hauptverfasser:	Tapolcsányi, Pál, Wölfling, János, Schneider, Gyula
Format:	Artikel
Sprache:	eng
Schlagworte:	16-Hydroxymethyl-5α-androstane-3β,17-diol Acetolysis Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Neighboring group participation Organic chemistry Preparations and properties Steroids Wagner-Meerwein rearrangement
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Zusammenfassung:	16α-Hydroxymethyl-5α-androstane-3β,17β-diol and 16β-hydroxymethyl-5α-androstane-3β,17β-diol, were obtained from reduction of 16-acetoxymethylene-5α-androstan-17-one. The corresponding 16α,17α- and 16β,17α-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.
ISSN:	0039-128X 1878-5867
DOI:	10.1016/S0039-128X(00)00237-3