Total synthesis of (-)-dysiherbaine

Chem Commun (Camb). 2012 Jun 25;48(50):6295-7. doi: 10.1039/c2cc32736h. Epub 2012 May 17.

Abstract

The enantioselective synthesis of (-)-dysiherbaine (1) has been established with efficiency via a unique synthetic strategy involving the desymmetrization of 2-substituted glycerol to install a quaternary chiral carbon, which induces further stereochemistry in the bicyclic perhydrofuropyran through mercuriocyclization and epoxidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alanine / analogs & derivatives*
  • Alanine / chemical synthesis
  • Alanine / chemistry
  • Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
  • Bridged Bicyclo Compounds, Heterocyclic / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Bridged Bicyclo Compounds, Heterocyclic
  • dysiherbaine
  • Alanine