A highly convergent approach toward (-)-brevenal

Org Lett. 2010 Jun 4;12(11):2614-7. doi: 10.1021/ol1008203.

Abstract

Progress toward a highly convergent, asymmetric synthesis of brevenal is reported. Construction of the AB-ring and E-ring cyclic ether fragments was achieved through asymmetric alkylation/ring-closing metathesis strategies. A Horner-Wadsworth-Emmons olefination was used in a key bond-forming step to couple the advanced cyclic fragments and enable rapid access to the AB-E ring system.

Publication types

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

MeSH terms

  • Alkylation
  • Catalysis
  • Dinoflagellida / chemistry
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Ethers / pharmacology
  • Marine Toxins / isolation & purification
  • Marine Toxins / toxicity
  • Molecular Structure
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Polymers / pharmacology
  • Stereoisomerism

Substances

  • Ethers
  • Marine Toxins
  • Polymers
  • brevenal (polyether)