Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids

…, JH Sattler, J Resch, P Macheroux…

Index: Schrittwieser, Joerg H.; Resch, Verena; Wallner, Silvia; Lienhart, Wolf-Dieter; Sattler, Johann H.; Resch, Jasmin; MacHeroux, Peter; Kroutil, Wolfgang Journal of Organic Chemistry, 2011 , vol. 76, # 16 p. 6703 - 6714

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Citation Number: 50

Abstract

A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C–C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic ...