Synthesis of cholestanes containing an oxygenated 14α-methyl group
- 1 January 1977
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 6,p. 700-702
- https://doi.org/10.1039/p19770000700
Abstract
Hydrocyanation of 3β-acetoxy-5α-cholest-8(14)-en-7-one has been achieved by reaction with diethylaluminium cyanide. The resulting 14α-cyano-7-ketone was reduced with sodium borohydride to the 7α-hydroxy-compound, the methanesulphonate of which, when refluxed in collidine, gave 3β-acetoxy-5α-cholest-7-ene-14α-carbonitrile. Reduction of the cyano-group with di-isobutylaluminium hydride afforded 3β-hydroxy-5α-cholest-7-ene-14α-carbaldehyde, which was transformed with lithium aluminium hydride into 14α-hydroxymethyl-5α-cholest-7-en-3β-ol.Keywords
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