Total synthesis of (8R,6'R)-peridinin-5,8-furanoxide

Chem Commun (Camb). 2013 Jun 4;49(44):5043-5. doi: 10.1039/c3cc41552j. Epub 2013 Apr 26.

Abstract

The first total synthesis of (8R,6'R)-peridinin-5,8-furanoxide, a C37 xanthophyll norcarotenoid, has been achieved. The key steps of the synthetic sequence are a Julia-Kocienski condensation and a late stage stereoretentive Stille cross-coupling of an iodoallene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carotenoids / chemical synthesis*
  • Carotenoids / chemistry
  • Catalysis
  • Epoxy Compounds / chemistry
  • Oxidation-Reduction
  • Stereoisomerism
  • Xanthophylls / chemistry*

Substances

  • Epoxy Compounds
  • Xanthophylls
  • peridinin
  • Carotenoids