Catalytic enantioselective approach to the stereodivergent synthesis of (+)-lasubines I and II

J Org Chem. 2007 Dec 21;72(26):10294-7. doi: 10.1021/jo702076j. Epub 2007 Nov 21.

Abstract

A concise and efficient approach to the stereodivergent synthesis of (+)-lasubines I and II is described. The key common intermediate is a chiral N-sulfonyl 2,3-dihydropyridone obtained by a novel Cu-catalyzed asymmetric formal aza-Diels-Alder reaction between N-tosyl aldimines and Danishefsky's diene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Molecular Conformation
  • Quinolizines / chemical synthesis*
  • Quinolizines / chemistry
  • Stereoisomerism

Substances

  • Quinolizines
  • lasubin I