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

Anass Znabet; Marloes M Polak; Elwin Janssen; Frans J J de Kanter; Nicholas J Turner; Romano V A Orru; Eelco Ruijter

doi:10.1039/c0cc02823a

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

Anass Znabet, Marloes M Polak, Elwin Janssen, Frans J J de Kanter, Nicholas J Turner, Romano V A Orru, Eelco Ruijter

Research output: Contribution to Journal › Article › Academic › peer-review

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.

Original language	English
Pages (from-to)	7918-7920
Number of pages	3
Journal	Chemical Commununications
Volume	46
Issue number	42
Early online date	20 Sept 2010
DOIs	https://doi.org/10.1039/c0cc02823a
Publication status	Published - 14 Nov 2010

Keywords

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

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title = "A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions",

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.",

keywords = "Antiviral Agents/chemical synthesis, Biocatalysis, Dimerization, Oligopeptides/chemical synthesis, Oxidation-Reduction, Serine Proteinase Inhibitors/chemical synthesis",

author = "Anass Znabet and Polak, {Marloes M} and Elwin Janssen and {de Kanter}, {Frans J J} and Turner, {Nicholas J} and Orru, {Romano V A} and Eelco Ruijter",

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T1 - A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions

AU - Znabet, Anass

AU - Polak, Marloes M

AU - Janssen, Elwin

AU - de Kanter, Frans J J

AU - Turner, Nicholas J

AU - Orru, Romano V A

AU - Ruijter, Eelco

PY - 2010/11/14

Y1 - 2010/11/14

N2 - 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.

AB - 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.

KW - Antiviral Agents/chemical synthesis

KW - Biocatalysis

KW - Dimerization

KW - Oligopeptides/chemical synthesis

KW - Oxidation-Reduction

KW - Serine Proteinase Inhibitors/chemical synthesis

U2 - 10.1039/c0cc02823a

DO - 10.1039/c0cc02823a

M3 - Article

C2 - 20856952

SN - 1359-7345

VL - 46

SP - 7918

EP - 7920

JO - Chemical Commununications

JF - Chemical Commununications

IS - 42

ER -

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

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Keywords

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