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

Kono M, Harada S, Nozaki T, et al. Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine. Organic letters. 2019;21(10):3750-3754.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