Chemoenzymatic access to enantiomeric bicyclo[2.2.1]heptan-2,5-diones

Bioorg Med Chem. 1994 Jun;2(6):493-500. doi: 10.1016/0968-0896(94)80019-7.

Abstract

A practical integrated process, combining an enzymatic resolution step with a few chemical transformations, is described for the synthesis of (1R, 4R)- and (2S, 4S)-bicyclo[2.2.1]heptan-2,5-diones 1 of high enantiomeric purity, starting from a standard mixture of (+/-)-endo- and exo-2-acetoxy-5-norbornene.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Candida / enzymology
  • Carbohydrate Conformation
  • Chromatography, Gas
  • Crystallization
  • Indicators and Reagents
  • Lipase*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Norbornanes / chemical synthesis*
  • Norbornanes / chemistry*
  • Norbornanes / isolation & purification
  • Optical Rotation
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Norbornanes
  • 2-acetoxy-5-norbornene
  • Lipase