Enantioselective synthesis of an octahydroindolizine (indolizidine) alcohol using an enzymatic resolution

Org Biomol Chem. 2017 Apr 5;15(14):2953-2961. doi: 10.1039/c7ob00192d.

Abstract

A homo-chiral synthesis of (7R,8aS)-octahydro-5,5-dimethylindolizin-7-amine 8 and (7S, 8aS)-octahydro-5,5-dimethylindolizin-7-ol 9, amine building blocks which have found applications within the pharmaceutical industry, is presented. The approach uses a Novozym 435-mediated kinetic resolution of racemic octahydroindolizine (indolizidine) alcohol 13 as a key step (up to 100 g scale).

MeSH terms

  • Alcohols / chemistry*
  • Biocatalysis
  • Chemistry Techniques, Synthetic
  • Enzymes, Immobilized
  • Fungal Proteins
  • Indolizidines / chemical synthesis*
  • Indolizidines / chemistry*
  • Kinetics
  • Lipase / metabolism*
  • Models, Molecular
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Alcohols
  • Enzymes, Immobilized
  • Fungal Proteins
  • Indolizidines
  • Novozyme 435
  • Lipase