A two-directional synthesis of (+/-)-perhydrohistrionicotoxin

J Org Chem. 2004 Mar 5;69(5):1598-602. doi: 10.1021/jo035639a.

Abstract

An entirely two-directional synthesis of (+/-)-perhydrohistrionicotoxin is presented, utilizing a tandem oxime formation/Michael addition/[3 + 2] cycloaddition as the key step. This approach also constitutes formal syntheses of (+/-)-histrionicotoxin and (+/-)-histrionicotoxin 235A.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amphibian Venoms / chemical synthesis*
  • Amphibian Venoms / chemistry
  • Amphibian Venoms / isolation & purification
  • Animals
  • Anura
  • Crystallography, X-Ray
  • Models, Molecular
  • Molecular Structure
  • Skin / chemistry
  • Stereoisomerism

Substances

  • Amphibian Venoms
  • perhydrohistrionicotoxin