Total synthesis of seco-plakortolide E and (-)-ent-plakortolide I: absolute configurational revision of natural plakortolide I

Org Lett. 2012 Jan 20;14(2):564-7. doi: 10.1021/ol203185f. Epub 2011 Dec 22.

Abstract

A first total synthesis of (-)-ent-plakortolide I and seco-plakortolide E was accomplished from (S)-2-methylglycidol. The relevant key reactions involve a diastereoselective Mukaiyama aldol reaction, a regioselective hydroperoxysilylation, and elaboration of the 1,2-dioxane ring by intramolecular Michael addition of a hydroperoxide group to a butenolide. This synthesis allowed the revision of the absolute configuration of plakortolide I and structural revision of plakortolide E.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • Biological Products / chemical synthesis*
  • Catalysis
  • Dioxanes / chemical synthesis*
  • Heterocyclic Compounds, 2-Ring / chemical synthesis*
  • Molecular Conformation
  • Peroxides / chemical synthesis*
  • Stereoisomerism

Substances

  • Biological Products
  • Dioxanes
  • Heterocyclic Compounds, 2-Ring
  • Peroxides
  • plakortolide E
  • plakortolide I
  • 4-Butyrolactone