First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol

Emily J. Westover, Douglas F. Covey

Research output: Contribution to journalArticle

27 Scopus citations

Abstract

We report the first synthesis of the unnatural enantiomer of desmosterol (ent-desmosterol). The sterol nucleus was constructed enantiospecifically, followed by stepwise addition of the side chain. Beginning with ent-androst-4-ene-3,17-dione, ent-desmosterol was synthesized in 13 steps and 20% yield. Protected ent-desmosterol was subjected to catalytic deuteration to afford ent-deuterocholesterol. Ent-desmosterol and ent-deuterocholesterol will be used to study the importance of sterol absolute configuration for sterol-lipid interactions in biophysical studies and in biological systems.

Original languageEnglish
Pages (from-to)159-166
Number of pages8
JournalSteroids
Volume68
Issue number2
DOIs
StatePublished - Feb 1 2003

Keywords

  • Enantiomers
  • Ent-cholesterol
  • Ent-desmosterol
  • Ent-deuterocholesterol
  • Sterols
  • Synthesis

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