An intramolecular aza-[3+3] annulation approach to azaphenalene alkaloids. Total synthesis of myrrhine

J Org Chem. 2007 Mar 30;72(7):2476-84. doi: 10.1021/jo062533h. Epub 2007 Mar 6.

Abstract

A detailed account on the stereoselective total syntheses of azaphenalene alkaloids via an intramolecular aza-[3+3] annulation strategy is described here. All five members of the Coccinellidae family of defensive alkaloids were prepared from the same common intermediate, which was derived from a stereoselective aza-[3+3] annulation reaction.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alkaloids / chemistry*
  • Aza Compounds / chemistry*
  • Carmine / analogs & derivatives*
  • Carmine / chemical synthesis
  • Carmine / chemistry
  • Lactams / chemistry
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Propanols / chemistry
  • Quinazolines / chemistry
  • Water / chemistry

Substances

  • Alkaloids
  • Aza Compounds
  • Lactams
  • Propanols
  • Quinazolines
  • hippodamine
  • myrrhine
  • Water
  • allyl alcohol
  • Carmine