A Concise Total Synthesis of (+)-Tetrabenazine and (+)-α-Dihydrotetrabenazine
- A Concise Total Synthesis of (+)-Tetrabenazine and (+)-α-Dihydrotetrabenazine
- 백승만; 김남중; 신동윤; 정재경; 정종화; 장동조; 문현영; 서영거
- bentazines; Claisen; rearrangement; total synthesis
- Issue Date
- Chemistry : a European journal
- VOL 16, 4623-4628
- 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.
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