A highly efficient synthesis of telaprevir by strategic use of biocatalysis and multicomponent reactions.
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.
Znabet
Anass
A
Department of Chemistry & Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands.
Polak
Marloes M
MM
Janssen
Elwin
E
de Kanter
Frans J J
FJ
Turner
Nicholas J
NJ
Orru
Romano V A
RV
Ruijter
Eelco
E
D000998:Antiviral Agents / Q000138:chemical synthesis*; D055162:Biocatalysis; D019281:Dimerization; D009842:Oligopeptides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D015842:Serine Proteinase Inhibitors / Q000138:chemical synthesis*
D000998:Antiviral Agents; D009842:Oligopeptides; D015842:Serine Proteinase Inhibitors; C486464:telaprevir