Total Synthesis and Absolute Configuration of (-)-Berkeleyamide A

Org Lett. 2010 Feb 5;12(3):420-3. doi: 10.1021/ol902525k.

Abstract

A chiral-pool approach to (-)-berkeleyamide A 1 based on a diastereoselective nitrile oxide [3 + 2]-cycloaddition completes the first total synthesis establishing the absolute stereochemistry of the natural product.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products / chemical synthesis*
  • Biological Products / chemistry*
  • Catalysis
  • Cyclization
  • Molecular Structure
  • Penicillium / chemistry
  • Pyrrolidinones / chemical synthesis*
  • Pyrrolidinones / chemistry*
  • Stereoisomerism

Substances

  • Biological Products
  • Pyrrolidinones
  • berkeleyamide A