Total synthesis of (-)-polycavernoside A: Suzuki-Miyaura coupling approach

Org Lett. 2012 Jun 15;14(12):3186-9. doi: 10.1021/ol301278e. Epub 2012 Jun 6.

Abstract

A total synthesis of (-)-polycavernoside A, a marine lethal toxin isolated from the edible alga Gracilaria edulis , has been achieved via a convergent approach. The synthesis is highlighted by catalytic asymmetric syntheses of the two key fragments and their union through Suzuki-Miyaura coupling and Keck macrolactonization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Disaccharides
  • Macrolides
  • polycavernoside A
  • polycavernoside B