The Ireland-Claisen rearrangement strategy towards the synthesis of the schizophrenia drug, (+)-asenapine

Org Biomol Chem. 2016 Jan 28;14(4):1332-7. doi: 10.1039/c5ob02047f. Epub 2015 Dec 11.

Abstract

(±)-Asenapine, sold in the market as Saphris/Sycrest for the treatment of bipolar disorders, is synthesized in an optically pure form involving an Ireland-Claisen rearrangement as the key step. This approach allows access to all diastereomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antipsychotic Agents / chemical synthesis*
  • Crystallography, X-Ray
  • Dibenzocycloheptenes
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Schizophrenia / drug therapy*
  • Stereoisomerism

Substances

  • Antipsychotic Agents
  • Dibenzocycloheptenes
  • Heterocyclic Compounds, 4 or More Rings
  • asenapine