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

Chem Commun (Camb)

Department of Chemistry & Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.

Published: November 2010

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.

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http://dx.doi.org/10.1039/c0cc02823aDOI Listing

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