Total synthesis of (-)-anamarine

J Org Chem. 2011 Aug 19;76(16):6889-93. doi: 10.1021/jo2010389. Epub 2011 Jul 22.

Abstract

Total synthesis of polyhydroxy δ-pyranone natural product (-)-anamarine is accomplished from D-(-)-tartaric acid. The main feature of the synthesis is the utility of hitherto unexplored β-keto phosphonate derived from tartaric acid amide and further elaboration involving stereoselective reduction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Products
  • Molecular Structure
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Stereoisomerism
  • Tartrates / chemistry*

Substances

  • Biological Products
  • Pyrones
  • Tartrates
  • anamarine
  • tartaric acid