Format

Send to

Choose Destination
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.

Author information

1
Graduate School of Pharmaceutical Sciences , Chiba University , 1-8-1, Inohana , Chuo-ku, Chiba 260-8675 , Japan.
2
Chair of Organic Chemistry I, Faculty of Chemistry , Bielefeld University , Universitätsstraße 25 , 33615 Bielefeld , Germany.
3
Graduate School of Pharmaceutical Sciences , Kyoto University , Yoshida, Sakyo-ku, Kyoto 606-8501 , Japan.
4
Graduate School of Pharmaceutical Sciences , Tokushima University , Shomachi, Tokushima 770-8505 , Japan.
5
Molecular Chirality Research Center , Chiba University , 1-33, Yayoi-cho , Inage-ku, Chiba 263-8522 , Japan.

Abstract

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.

Supplemental Content

Full text links

Icon for American Chemical Society
Loading ...
Support Center