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A Ring-Closing Metathesis-Based Approach to the Synthesis of (+)-Tetrabenazine

Author:
Johannes, Manuel, Altmann, Karl-Heinz
Source:
Organic letters 2012 v.14 no.14 pp. 3752-3755
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, organic compounds, stereoselective synthesis
Abstract:
A modular stereoselective synthesis of the vesicular monoamine transport inhibitors (+)-tetrabenazine ((+)-1) and (+)-α-dihydrotetrabenazine ((+)-2) has been developed. The approach is based on amine 4 and acid 5 as the key building blocks, which were elaborated into macrolactam 3 by amide coupling and a subsequent highly E-selective RCM reaction. Macrolactam 3 could be converted into tetrabenazine in three known steps.
Agid:
5784104