Total synthesis of brevetoxin A

Org Lett. 2009 Jan 15;11(2):489-92. doi: 10.1021/ol802710u.

Abstract

A total synthesis of brevetoxin A is reported. Two tetracyclic coupling partners, prepared from previously reported advanced fragments, were effectively united via a Horner-Wittig olefination. The resulting octacycle was progressed to substrates that were explored for reductive etherification, the success of which led to a penultimate tetraol intermediate. The tetraol was converted to the natural product through an expeditious selective oxidative process followed by methylenation.

Publication types

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

MeSH terms

  • Aldehydes / chemistry
  • Alkenes / chemistry
  • Marine Toxins / chemical synthesis*
  • Marine Toxins / chemistry
  • Oxidation-Reduction
  • Oxocins / chemical synthesis*
  • Oxocins / chemistry
  • Substrate Specificity

Substances

  • Aldehydes
  • Alkenes
  • Marine Toxins
  • Oxocins
  • Brevetoxin A