A Concise Total Synthesis of (+)-Tetrabenazine and (+)-α-Dihydrotetrabenazine

Title
A Concise Total Synthesis of (+)-Tetrabenazine and (+)-α-Dihydrotetrabenazine
Authors
백승만김남중신동윤정재경정종화장동조문현영서영거
Keywords
bentazines; Claisen; rearrangement; total synthesis
Issue Date
2010-04
Publisher
Chemistry : a European journal
Citation
VOL 16, 4623-4628
Abstract
Highly concise asymmetric total syntheses of (+)-tetrabenazine (1), a drug for the treatment of chorea associated with Huntington s disease, and of (+)- α-dihydrotetrabenazine (2), an active metabolite of 1, have been accomplished. Our synthetic route features a trans-selective enol etherification, followed by an unprecedented cation-dependent aza-Claisen rearrangement to establish the carbon framework and two stereogenic centers of tetrabenazine. The syntheses consist of seven steps (34% overall yield) for (+)-2 and eight steps (22% overall yield) for (+)-1.
URI
http://pubs.kist.re.kr/handle/201004/45591
ISSN
0947-6539
Appears in Collections:
KIST Publication > Article
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