Synthesis of 5α-Cholestan-6-one Derivatives with Some Substituents at the C-1, C-2, or C-3 Position(Organic,Chemical)

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Author(s)

Abstract

In order to investigate the regioselectivity of Baeyer-Villiger oxidation, thirty 5α-cholestan-6-one derivatives with various substituents (methyl, hydrogen, acetoxymethyl, methoxy, acetyloxy, benzoyloxy, trifluoroacetyloxy, p-toluenesulfonyloxy) at the C-1, C-2, or C-3 position were synthesized from cholesterol. The 6-oxo functional group of 5α-cholestan-6-one derivatives was introduced via hydroboration. The 3β-derivatives were readily obtained by using the native 3β-hydroxyl group of cholesterol. The 3α-isomers were obtained by inversion of the configuration of the 3β-tosylate 24 with tetra-n-butylammonium acetate in refluxing 2-butanone. The 2β-isomers were derived from the 2-ene 43 by bromohydrination, LiAlH_4 reduction, and esterification. The 2β-to 2α-hydroxyl group inversion was achieved by Birch reduction of the 2-oxo steroid 51. The 1α-derivatives were derived from the known 6β-acetoxy-la-hydroxy-5α-cholest-2-ene (57).

Journal

  • Chem. Pharm. Bull.

    Chem. Pharm. Bull. 35, 986-995, 1987

    The Pharmaceutical Society of Japan

Cited by:  1

Codes

  • NII Article ID (NAID)
    110006281006
  • NII NACSIS-CAT ID (NCID)
    AA00602100
  • Text Lang
    ENG
  • Article Type
    Journal Article
  • ISSN
    00092363
  • Data Source
    CJPref  NII-ELS 
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