The Journal of organic chemistry

Formal total synthesis of the potent renin inhibitor aliskiren: application of a SmI2-promoted acyl-like radical coupling

KB Lindsay, T Skrydstrup

Index: Lindsay, Karl B.; Skrydstrup, Troels Journal of Organic Chemistry, 2006 , vol. 71, # 13 p. 4766 - 4777

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Citation Number: 56

Abstract

A formal total synthesis of the potent renin inhibitor aliskiren is disclosed exploiting an alternative coupling strategy recently developed by this laboratory for the preparation of the hydroxyethylene isostere-based class of protease inhibitors. The thioester derivative of the amino acid representing the C5-C9 fragment of the aliskiren carbon skeleton underwent a carbon chain extension via a SmI2-promoted radical addition to n-butyl acrylate. ...