Asymmetric total synthesis of (+)-fumimycin via 1,2-addition to ketimines

Chem Commun (Camb). 2010 Dec 28;46(48):9215-7. doi: 10.1039/c0cc03399e. Epub 2010 Oct 28.

Abstract

The first asymmetric total synthesis of fumimycin was accomplished. As a key step, a 1,2-addition of methyl Grignard reagents to ketimines with quinine as additive was employed. The absolute configuration of (+)-fumimycin was determined by CD-spectroscopy combined with time-dependent density functional calculations.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Benzofurans / chemical synthesis*
  • Imines / chemistry*
  • Models, Molecular
  • Nitriles / chemistry*
  • Quinine
  • Spectrum Analysis
  • Stereoisomerism

Substances

  • Benzofurans
  • Imines
  • Nitriles
  • fumimycin
  • ketimine
  • Quinine