Total synthesis of (-)-strychnine

Yosuke Kaburagi; Hidetoshi Tokuyama; Tohru Fukuyama

doi:10.1021/ja046407b

Total synthesis of (-)-strychnine

J Am Chem Soc. 2004 Aug 25;126(33):10246-7. doi: 10.1021/ja046407b.

Authors

Yosuke Kaburagi¹, Hidetoshi Tokuyama, Tohru Fukuyama

Affiliation

¹ Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 15315428
DOI: 10.1021/ja046407b

Abstract

Total synthesis of (-)-strychnine is described. Notable features of our synthesis include (1) palladium-catalyzed coupling of the indole and vinyl epoxide moieties, (2) synthesis of the nine-membered cyclic amine derivative from the diol precursor in a one-pot procedure, and (3) transannular cyclization of the nine-membered cyclic amine.

Publication types

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

MeSH terms

Poisons / chemical synthesis
Poisons / chemistry
Stereoisomerism
Strychnine / chemical synthesis*
Strychnine / chemistry

Substances

Poisons
Strychnine