Total synthesis of (+)-kalkitoxin

Chem Commun (Camb). 2003 Aug 21:(16):2012-3.

Abstract

The neurotoxic lipopeptide (+)-kalkitoxin was synthesized by a route which employed asymmetric organocopper conjugate addition followed by in situ enolate alkylation to install the anti,anti-1,2,4-trimethyl relationship of the toxin; the synthesis of kalkitoxin required sixteen steps and proceeded in 3% overall yield.

Publication types

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

MeSH terms

  • Crystallography, X-Ray
  • Lipids / chemical synthesis*
  • Lipids / chemistry
  • Lipoproteins / chemical synthesis
  • Lipoproteins / chemistry
  • Models, Chemical
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Neurotoxins / chemical synthesis
  • Neurotoxins / chemistry
  • Stereoisomerism
  • Thiazoles / chemical synthesis*
  • Thiazoles / chemistry

Substances

  • Lipids
  • Lipoproteins
  • Neurotoxins
  • Thiazoles
  • kalkitoxin