Paek, Seung-Mann Kim, Nam-Jung Shin, Dongyun Jung, Jae-Kyung Jung, Jong-Wha Chang, Dong-Jo Moon, Hyunyoung Suh, Young-Ger 2024-01-20T19:33:00Z 2024-01-20T19:33:00Z 2021-09-02 2010-04 0947-6539 https://pubs.kist.re.kr/handle/201004/131585 Highly concise asymmetric total syntheses of (+)-tetrabenazine (1), a drug for the treatment of chorea associated with Huntington's disease, and of (+)-alpha-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. English WILEY-V C H VERLAG GMBH STEREOCONTROLLED TOTAL-SYNTHESIS AZA-CLAISEN REARRANGEMENT ASYMMETRIC-SYNTHESIS ACYL-CLAISEN ENOL ETHERS TETRABENAZINE EFFICIENT LACTAMS BINDING DRUG A Concise Total Synthesis of (+)-Tetrabenazine and (+)-alpha-Dihydrotetrabenazine Article 10.1002/chem.200902591 1 CHEMISTRY-A EUROPEAN JOURNAL, v.16, no.15, pp.4623 - 4628 CHEMISTRY-A EUROPEAN JOURNAL 16 15 4623 4628 scie scopus 000277331000023 2-s2.0-77950818724 Chemistry, Multidisciplinary Chemistry Article STEREOCONTROLLED TOTAL-SYNTHESIS AZA-CLAISEN REARRANGEMENT ASYMMETRIC-SYNTHESIS ACYL-CLAISEN ENOL ETHERS TETRABENAZINE EFFICIENT LACTAMS BINDING DRUG bentazines Claisen rearrangement rearrangement total synthesis