First total synthesis and stereochemical definition of isodomoic acid G

Org Lett. 2003 Oct 2;5(20):3771-3. doi: 10.1021/ol0355783.

Abstract

[structure: see text] The first total synthesis and stereochemical definition of isodomoic acid G has been achieved. The key nickel-catalyzed coupling of an alkynyl enone with an alkenylzirconium allows formation of the pyrrolidine ring and most of the stereochemical features in a single step. This report provides the first total synthesis application of this new reaction and illustrates its utility in the stereoselective preparation of highly substituted 1,3-dienes.

Publication types

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

MeSH terms

  • Kainic Acid / analogs & derivatives*
  • Kainic Acid / chemical synthesis*
  • Kainic Acid / chemistry
  • Organometallic Compounds / chemistry
  • Pyrrolidines / chemistry
  • Stereoisomerism
  • Zirconium / chemistry

Substances

  • Organometallic Compounds
  • Pyrrolidines
  • Zirconium
  • pyrrolidine
  • domoic acid
  • Kainic Acid