Formal synthesis of leustroducsin B via Reformatsky/Claisen condensation of silyl glyoxylates

Org Lett. 2011 Jun 17;13(12):3206-9. doi: 10.1021/ol2011192. Epub 2011 May 17.

Abstract

A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched β-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishi's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glyoxylates / chemistry*
  • Lactones / chemical synthesis
  • Lactones / chemistry
  • Molecular Structure
  • Organophosphorus Compounds / chemical synthesis
  • Organophosphorus Compounds / chemistry
  • Organosilicon Compounds / chemistry*
  • Pyrones

Substances

  • Glyoxylates
  • Lactones
  • Organophosphorus Compounds
  • Organosilicon Compounds
  • Pyrones
  • leustroducsin B