Total synthesis of (-)-goniotrionin

J Org Chem. 2012 Apr 20;77(8):4046-62. doi: 10.1021/jo3004106. Epub 2012 Apr 3.

Abstract

A stereoselective total synthesis of the reported structure of goniotrionin (4) has been accomplished. The key steps involved the opening of a chiral epoxide, a highly diastereoselective Mukaiyama aerobic oxidative cyclization, a selective 1,2-syn Mukaiyama aldol reaction, and a Noyori reduction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Epoxy Compounds / chemistry*
  • Furans / chemical synthesis*
  • Furans / chemistry*
  • Lactones / chemical synthesis*
  • Lactones / chemistry*
  • Molecular Structure
  • Oxidation-Reduction
  • Stereoisomerism

Substances

  • Epoxy Compounds
  • Furans
  • Lactones
  • goniotrionin