Synthesis of (-)-agelastatin A by [3.3] sigmatropic rearrangement of allyl cyanate

Org Lett. 2007 Aug 2;9(16):2989-92. doi: 10.1021/ol0709735. Epub 2007 Jun 30.

Abstract

Total synthesis of (-)-agelastatin A has been achieved starting from l-arabitol. The highlights in our synthesis include the preparation of vicinal diamine moiety by [3.3] sigmatropic rearrangement of allyl cyanate and construction of central ring-C with ring-closing metathesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemical synthesis*
  • Alkaloids / chemistry
  • Allyl Compounds / chemistry*
  • Catalysis
  • Cyanates / chemistry*
  • Molecular Structure
  • Oxazolidinones / chemical synthesis*
  • Oxazolidinones / chemistry
  • Stereoisomerism
  • Sugar Alcohols / chemistry*

Substances

  • Alkaloids
  • Allyl Compounds
  • Cyanates
  • Oxazolidinones
  • Sugar Alcohols
  • agelastatin A
  • arabitol