Literature DB >> 870213

Sterol synthesis. Chemical synthesis of 3beta-benzoyloxy -14alpha, 15alpha-epoxy-5alpha-cholest-7-ene, a key intermediate in the synthesis of 15-oxygenated sterols.

E J Parish, T E Spike, G J Schroepfer.   

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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Year:  1977        PMID： 870213     DOI： 10.1016/0009-3084(77)90011-1

Source DB:  PubMed          Journal:  Chem Phys Lipids        ISSN： 0009-3084            Impact factor:   3.329


  4 in total

1.  Syntheses of ring C oxysterols: inhibitors of sterol biosynthesis.

Authors:  Edward J Parish; Chi Luo; Thomas Webb; John D Gorden
Journal:  Lipids       Date:  2007-01-16       Impact factor: 1.880

2.  5 alpha-Cholest-8(14)-en-3 beta-ol-15-one, a potent inhibitor of sterol biosynthesis, lowers serum cholesterol and alters distributions of cholesterol in lipoproteins in baboons.

Authors:  G J Schroepfer; E J Parish; A Kisic; E M Jackson; C M Farley; G E Mott
Journal:  Proc Natl Acad Sci U S A       Date:  1982-05       Impact factor: 11.205

3.  5 alpha-Cholest-8(14)-en-3 beta-ol-15-one lowers serum cholesterol and induces profound changes in the levels of lipoprotein cholesterol and apoproteins in monkeys fed a diet of moderate cholesterol content.

Authors:  G J Schroepfer; B C Sherrill; K S Wang; W K Wilson; A Kisic; T B Clarkson
Journal:  Proc Natl Acad Sci U S A       Date:  1984-11       Impact factor: 11.205

4.  Oxysterols: chemical synthesis, biosynthesis and biological activities.

Authors:  E J Parish; V B Nanduri; H H Kohl; F R Taylor
Journal:  Lipids       Date:  1986-01       Impact factor: 1.880
  4 in total

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