Chemoenzymatic asymmetric total synthesis of (S)-Rivastigmine using omega-transaminases

Chem Commun (Camb). 2010 Aug 14;46(30):5500-2. doi: 10.1039/c0cc00585a. Epub 2010 May 11.

Abstract

A straightforward, high-yielding, chemoenzymatic total synthesis of enantiopure (S)-Rivastigmine was developed using various omega-transaminases for the asymmetric amination of appropriate acetophenone precursors. Optimisation of the biotransformation allowed scale-up and the total synthesis of (S)-Rivastigmine.

MeSH terms

  • Acetophenones / chemistry
  • Bacteria / enzymology*
  • Neuroprotective Agents / chemical synthesis*
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / metabolism
  • Phenylcarbamates / chemical synthesis*
  • Phenylcarbamates / chemistry
  • Phenylcarbamates / metabolism
  • Rivastigmine
  • Stereoisomerism
  • Transaminases / metabolism*

Substances

  • Acetophenones
  • Neuroprotective Agents
  • Phenylcarbamates
  • Transaminases
  • Rivastigmine
  • acetophenone