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  • Title: Sterol synthesis. Chemical synthesis of 3beta-benzoyloxy -14alpha, 15alpha-epoxy-5alpha-cholest-7-ene, a key intermediate in the synthesis of 15-oxygenated sterols.
    Author: Parish EJ, Spike TE, Schroepfer GJ.
    Journal: Chem Phys Lipids; 1977 Apr; 18(3-4):233-9. PubMed ID: 870213.
    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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