Stereoselective Tandem Synthesis of Pyrrolidine Derivatives under Gold Catalysis: An Asymmetric Synthesis of (-)-Lepadiformine A

Atsushi Yoshimura; Ryohei Hanzawa; Haruhiko Fuwa

doi:10.1021/acs.orglett.2c02007

Stereoselective Tandem Synthesis of Pyrrolidine Derivatives under Gold Catalysis: An Asymmetric Synthesis of (-)-Lepadiformine A

Org Lett. 2022 Sep 2;24(34):6237-6241. doi: 10.1021/acs.orglett.2c02007. Epub 2022 Jul 18.

Authors

Atsushi Yoshimura¹, Ryohei Hanzawa¹, Haruhiko Fuwa¹

Affiliation

¹ Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

PMID: 35849685
DOI: 10.1021/acs.orglett.2c02007

Abstract

A Au-catalyzed tandem alkyne hydroamination/iminium ion formation/allylation reaction was developed for expedient access to pyrrolidine derivatives bearing a tetrasubstituted carbon stereocenter. The tandem reaction was successfully applied to a 12-step asymmetric synthesis of (-)-lepadiformine A, a marine cytotoxic tricyclic alkaloid.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids*
Catalysis
Gold*
Molecular Structure
Pyrrolidines
Stereoisomerism

Substances

Alkaloids
Pyrrolidines
lepadiformine
Gold