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

Steroids. 2017 May:121:22-31. doi: 10.1016/j.steroids.2017.03.002. Epub 2017 Mar 12.

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.

Keywords: Cross-metathesis; Grubbs catalyst; Ruthenium catalyst; Side-chain oxysterols; ent-steroids; Δ(22)-steroids.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Molecular Structure
  • Oxysterols / chemistry*
  • Ruthenium / chemistry
  • Stereoisomerism
  • Steroids / chemistry*

Substances

  • Oxysterols
  • Steroids
  • Ruthenium