Neighboring group participation. Part 14. The preparation of the four stereoisomers of 16-hydroxymethyl-5alpha-androstane-3beta,17-diol. |
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| Authors: | P Tapolcsányi J W?lfling G Schneider |
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| Affiliation: | Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720, Szeged, Hungary. |
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| Abstract: | 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. |
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