doi: 10.1016/0009-3084(77)90011-1.
Sterol synthesis. Chemical synthesis of 3beta-benzoyloxy -14alpha, 15alpha-epoxy-5alpha-cholest-7-ene, a key intermediate in the synthesis of 15-oxygenated sterols
- PMID: 870213
- DOI: 10.1016/0009-3084(77)90011-1
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Sterol synthesis. Chemical synthesis of 3beta-benzoyloxy -14alpha, 15alpha-epoxy-5alpha-cholest-7-ene, a key intermediate in the synthesis of 15-oxygenated sterols
Chem Phys Lipids.
1977 Apr.
Abstract
3BETA-Benzoyloxy-14alpha, 15alpha-cholest-7-ene was obtained in 96% yield upon treatment of 3beta-benzoyloxy-5alpha-cholesta-7, 14-diene with m-chloroperbenzoic acid. The delta7-14alpha, 15alpha-epoxy-steryl ester provides a useful intermediate for the syntheses of sterols with an oxygen function at carbon atom 15. For example, treatment of 3beta-benzoyloxy-14alpha, 15alpha-epoxy-5alpha-cholest-7-ene with methanolic hydrochloric acid gave 3beta-benzoyloxy-5alpha-cholest-8(14)-en-15-one in 82% yield.
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