A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions

Chem Commun (Camb). 2010 Nov 14;46(42):7918-20. doi: 10.1039/c0cc02823a. Epub 2010 Sep 20.

Abstract

A very short and efficient synthesis of the important drug candidate telaprevir, featuring a biocatalytic desymmetrization and two multicomponent reactions as the key steps, is presented. The classical issue of lack of stereoselectivity in Ugi- and Passerini-type reactions is circumvented. The atom economic and convergent nature of the synthetic strategy require only very limited use of protective groups.

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Biocatalysis
  • Dimerization
  • Oligopeptides / chemical synthesis*
  • Oxidation-Reduction
  • Serine Proteinase Inhibitors / chemical synthesis*

Substances

  • Antiviral Agents
  • Oligopeptides
  • Serine Proteinase Inhibitors
  • telaprevir