A new method for the preparation of Ent-cholesterol from Ent- testosterone

A. Sampath Kumar, Douglas F. Covey

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C21l 3-silyloxy-Δ(5,17(20))-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant Δ16 double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent- testosterone.

Original languageEnglish
Pages (from-to)823-826
Number of pages4
JournalTetrahedron Letters
Volume40
Issue number5
DOIs
StatePublished - Jan 29 1999

Keywords

  • Enantiospecificity
  • Ene reactions
  • Stereocontrol
  • Steroids and Sterols

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