1. Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine
- Author
-
Kiyosei Takasu, Tetsuhiro Nemoto, Yasumasa Hamada, Yoshinori Hashimoto, Shingo Harada, Yusuke Kuroda, Harald Gröger, Ken-ichi Yamada, Masato Kono, Shun-ichi Murata, and Tomoyuki Nozaki
- Subjects
organic chemicals ,Organic Chemistry ,Enantioselective synthesis ,Catharanthine ,Biochemistry ,Chemical synthesis ,Desymmetrization ,Combinatorial chemistry ,Catalysis ,Formal synthesis ,chemistry.chemical_compound ,chemistry ,Insertion reaction ,Amide ,polycyclic compounds ,heterocyclic compounds ,Physical and Theoretical Chemistry - 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.
- Published
- 2019