Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids

David P. Brownholland, Douglas F. Covey

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

A synthetic route that utilizes a cross-metathesis reaction with Δ22 steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.

Original languageEnglish
Pages (from-to)22-31
Number of pages10
JournalSteroids
Volume121
DOIs
StatePublished - Jan 1 2017

Keywords

  • Cross-metathesis
  • Grubbs catalyst
  • Ruthenium catalyst
  • Side-chain oxysterols
  • ent-steroids
  • Δ-steroids

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