Organic Process Research and Development p. 377 - 384 (2018)
Update date:2022-08-15
Topics:
Xu, Hua
Wang, Fang
Xue, Weicai
Zheng, Yunjie
Wang, Qi
Qiu, Fayang G.
Jin, Yehua
A practical synthetic route for pilot production of entecavir is described. It is safe, robust, and scalable to kilogram scale. Starting from (S)-(+)-carvone, this synthetic route consists of a series of highly efficient reactions including a Favorskii rearrangement-elimination-epimerization sequence to establish the cyclopentene skeleton, the Baeyer-Villiger oxidation/rearrangement to afford the correct configuration of the secondary alcohol, and a directed homoallylic epoxidation followed by epoxide ring-opening to introduce the hydroxyl group suitable for the Mitsunobu reaction. In addition, the synthesis contains only four brief chromatographic purifications.
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