Lipase-catalyzed domino kinetic resolution of alpha-hydroxynitrones/intramolecular 1,3-dipolar cycloaddition: a concise asymmetric total synthesis of (-)-rosmarinecine

Chem Commun (Camb). 2005 May 14:(18):2369-71. doi: 10.1039/b419426h. Epub 2005 Mar 16.

Abstract

The title domino reactions were developed to directly provide tetrahydrofuro[3,4-c]isoxazole derivatives (5 and 9) in > or =90% ee from racemic alpha-hydroxynitrones (2 and 6), which were used in the concise asymmetric total synthesis of (-)-rosmarinecine .

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Imines / chemistry*
  • Kinetics
  • Lipase / chemistry*
  • Molecular Conformation
  • Pyrrolizidine Alkaloids / chemical synthesis*
  • Pyrrolizidine Alkaloids / chemistry
  • Stereoisomerism

Substances

  • Imines
  • Pyrrolizidine Alkaloids
  • rosmarinecine
  • Lipase