Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 10, Pages 4001-4004Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo900480n
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- GE Healthcare Medical Diagnostics
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The enantioselective synthesis of (+)-tetrabenazine (TBZ) and (+)-dihydrotetrabenazine (DTBZ), agents of significant interest for therapeutic and molecular imaging applications, has been completed in 21% (TBZ) and 16% (DTBZ) overall yield and in > 97% ee from the starting dihydroisoquinoline. The synthesis utilizes Sodeoka's palladium-catalyzed asymmetric malonate addition to set the initial stereocenter followed by a number of diastereoselective transformations to incorporate the remaining asymmetric centers.
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