Efficient syntheses of the keto-carotenoids canthaxanthin, astaxanthin, and astacene

J Org Chem. 2005 Apr 15;70(8):3328-31. doi: 10.1021/jo050101l.

Abstract

Three keto-carotenoids were prepared by the oxidation of the stable C(40) trisulfone 6, which has been used as the key compound in our beta-carotene synthesis. The first allylic oxidation to the unsaturated ketone and the second oxidation to the alpha-hydroxyketone produced the C(40) trisulfones 7 and 10, respectively. The Ramberg-Backlund reaction of the oxidized C(40) trisulfone was efficiently effected by the use of a mild base, NaOMe, in the presence of CCl(4) as a halogenating agent to give the C(40) disulfones 8 and 11. Base-promoted dehydrosulfonation reaction of the disulfone compounds produced the fully conjugated polyenes of canthaxanthin (1), astaxanthin (2), and astacene (3).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Canthaxanthin / chemical synthesis*
  • Carotenoids / chemical synthesis*
  • Combinatorial Chemistry Techniques*
  • Molecular Structure
  • Oxidation-Reduction
  • Xanthophylls
  • beta Carotene / analogs & derivatives*
  • beta Carotene / chemical synthesis*

Substances

  • Xanthophylls
  • astacene
  • beta Carotene
  • Carotenoids
  • Canthaxanthin
  • astaxanthine