Total synthesis of Tasimelteon

[Display omitted] •A chiral approach has been accomplished for the total synthesis of Tasimelteon.•Tasimelteon is effective for treatment of non-24-h sleep-wake disorder.•The synthesis was accomplished in four steps in overall 48% yield.•This synthetic method is beneficial to industrial production....

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Bibliographic Details
Published in:Tetrahedron letters 2019-07, Vol.60 (30), p.1986-1988
Main Authors: Li, Xi-An, Yue, Lirong, Zhu, Jianrong, Ren, Huazhong, Zhang, Hong, Hu, Dong-yan, Han, Guangtian, Feng, Jiafu, Nan, Ze-dong
Format: Article
Language:English
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Accomplished
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Tasimelteon
Total synthesis
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Summary:[Display omitted] •A chiral approach has been accomplished for the total synthesis of Tasimelteon.•Tasimelteon is effective for treatment of non-24-h sleep-wake disorder.•The synthesis was accomplished in four steps in overall 48% yield.•This synthetic method is beneficial to industrial production. A simple and efficient approach has been accomplished for the total synthesis of active pharmaceutical ingredient (API) of Tasimelteon which is effective for treatment of non-24-h sleep-wake disorder. Starting from 4-vinyl-2, 3-dihydrobenzofuran, the synthesis involves asymmetric epoxidation, Wittig reaction, reduction of the nitrile group and propionation of the amine. The synthesis was accomplished in four steps in overall 48% yield.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.06.048