Cobalt-catalyzed diastereoselective synthesis of C-furanosides. Total synthesis of (-)-isoaltholactone

J Org Chem. 2013 Dec 6;78(23):11807-14. doi: 10.1021/jo401845q. Epub 2013 Nov 12.

Abstract

An array of C-aryl and C-vinyl furanosides were prepared in good yields and diastereoselectivities from C-halogeno furanosides either with aryl Grignard or with vinyl Grignard using the convenient Co(acac)3/TMEDA catalytic system. This method is illustrated by the total synthesis of the (-)-isoaltholactone.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cobalt / chemistry*
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Molecular Conformation
  • Organometallic Compounds / chemistry*
  • Pyrones / chemistry

Substances

  • Furans
  • Organometallic Compounds
  • Pyrones
  • altholactone
  • Cobalt