Total synthesis of (-)-pironetin

Org Lett. 2003 Feb 6;5(3):265-8. doi: 10.1021/ol027211o.

Abstract

[structure: see text] The asymmetric total synthesis of pironetin, a compound that shows plant growth regulatory activity, immunosuppressive as well as a remarkable antitumoral activity, is described. The approach involves the use of three very efficient Evans oxazolidinone-mediated syn-aldol condensations, a high-yielding coupling between lithium acetylide ethylenediamine complex and a tosylate followed by methylation, and selective reduction to establish the C12-C13 (E) double bond.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Molecular Structure
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry

Substances

  • Pyrones
  • pironetin