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Org Lett. 2019 May 17;21(10):3750-3754. doi: 10.1021/acs.orglett.9b01198. Epub 2019 Apr 25.

Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine.

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Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1, Inohana , Chuo-ku, Chiba 260-8675 , Japan.
Chair of Organic Chemistry I, Faculty of Chemistry , Bielefeld University , Universitätsstraße 25 , 33615 Bielefeld , Germany.
Graduate School of Pharmaceutical Sciences , Kyoto University , Yoshida, Sakyo-ku, Kyoto 606-8501 , Japan.
Graduate School of Pharmaceutical Sciences , Tokushima University , Shomachi, Tokushima 770-8505 , Japan.
Molecular Chirality Research Center , Chiba University , 1-33, Yayoi-cho , Inage-ku, Chiba 263-8522 , Japan.


Although (+)-catharanthine is an attractive alkaloid for both clinical research and organic synthetic chemistry, only a limited number of approaches for its catalytic asymmetric synthesis exist. Herein, we describe a novel strategy for synthesizing a chiral intermediate of (+)-catharanthine via phosphoric acid-catalyzed asymmetric desymmetrization of a meso-isoquinuclidine possessing a 1,3-diol unit that was synthesized by a formal amide insertion reaction.

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