Synthesis of symmetrical carotenoids by a two-fold Stille reaction

J Org Chem. 2002 Jul 12;67(14):5040-3. doi: 10.1021/jo025727f.

Abstract

beta-Carotene 1 and (3R,3'R)-zeaxanthin 2 have been stereoselectively prepared in a highly convergent fashion by a 2-fold Stille cross-coupling reaction. The C(12)-pentaenylbis-stannane 8 is the central "lynchpin" that connects two units of the terminal C(14)-iodides 9 and 17 to afford 1 and 2, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carotenoids / chemical synthesis*
  • Carotenoids / chemistry
  • Catalysis
  • Chemistry, Organic / methods
  • Iodides / chemistry
  • Molecular Structure
  • Stereoisomerism
  • Tin Compounds / chemistry*
  • Xanthophylls
  • Zeaxanthins
  • beta Carotene / analogs & derivatives*
  • beta Carotene / chemical synthesis

Substances

  • Iodides
  • Tin Compounds
  • Xanthophylls
  • Zeaxanthins
  • beta Carotene
  • Carotenoids