Efficient convergent synthesis of 1alpha,25-dihydroxyvitamin D3 and its analogues by Suzuki-Miyaura coupling

Org Lett. 2003 Feb 20;5(4):523-5. doi: 10.1021/ol0274007.

Abstract

[reaction: see text] 1alpha,25-Dihydroxyvitamin D(3) was synthesized by the Suzuki-Miyaura coupling of the A-ring intermediate 1, which was efficiently prepared from readily available 1,7-enyne 2, with the corresponding boronate compound of the C,D-ring portion. The method was applied to prepare des-C,D analogues of 1alpha,25-dihydroxyvitamin D(3).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry
  • Boranes
  • Calcitriol / analogs & derivatives
  • Calcitriol / chemical synthesis*
  • Cyclization
  • Epichlorohydrin / chemistry
  • Lithium Compounds

Substances

  • Alkynes
  • Boranes
  • Lithium Compounds
  • Epichlorohydrin
  • boron trifluoride
  • Calcitriol