An asymmetric total synthesis of brevisamide

Org Lett. 2009 Sep 17;11(18):4164-7. doi: 10.1021/ol901691d.

Abstract

An enantioselective synthesis of marine alkaloid brevisamide was accomplished in a convergent manner. The synthesis utilized an enantioselective hetero-Diels-Alder reaction which sets three chiral centers in compound 11. The synthesis also features a modified Wolff-Kishner reduction, Rubottom oxidation, and Suzuki-Miyaura coupling to furnish brevisamide.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemical synthesis*
  • Fatty Acids, Unsaturated / chemical synthesis*
  • Marine Biology
  • Molecular Structure
  • Pyrans
  • Stereoisomerism*

Substances

  • Alkaloids
  • Fatty Acids, Unsaturated
  • Pyrans
  • brevisamide