Total synthesis of fostriecin: via a regio- and stereoselective polyene hydration, oxidation, and hydroboration sequence

Org Lett. 2010 Sep 3;12(17):3752-5. doi: 10.1021/ol101340n.

Abstract

A total synthesis of the fostriecin has been achieved in 24 steps from enyne 11. The lactone moiety was installed by a Leighton allylation and Grubbs ring-closing metathesis reaction. The highly reactive Z,Z,E-triene moiety was installed via a late-stage Suzuki-Miyaura cross-coupling of a remarkably stable Z-vinyl boronate. The relative and absolute stereocenters of the C-8,9,11 triol were generated with a regio- and stereoselective asymmetric hydration/oxidation sequence.

Publication types

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

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Polyenes / chemical synthesis*
  • Polyenes / chemistry
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Stereoisomerism
  • Streptomyces / chemistry

Substances

  • Biological Products
  • Polyenes
  • Pyrones
  • fostriecin