ol9b01198_si_001.pdf (1.58 MB)
Asymmetric Formal Synthesis of (+)-Catharanthine via Desymmetrization of Isoquinuclidine
Version 2 2019-04-29, 14:38
Version 1 2019-04-25, 14:05
journal contribution
posted on 2019-04-25, 00:00 authored by Masato Kono, Shingo Harada, Tomoyuki Nozaki, Yoshinori Hashimoto, Shun-ichi Murata, Harald Gröger, Yusuke Kuroda, Ken-ichi Yamada, Kiyosei Takasu, Yasumasa Hamada, Tetsuhiro NemotoAlthough (+)-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.