Total synthesis of (-)-galanthamine and (-)-lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive Heck cyclization

Ji-Qiang Chen; Jian-Hua Xie; Deng-Hui Bao; Sheng Liu; Qi-Lin Zhou

doi:10.1021/ol300913g

Total synthesis of (-)-galanthamine and (-)-lycoramine via catalytic asymmetric hydrogenation and intramolecular reductive Heck cyclization

Org Lett. 2012 Jun 1;14(11):2714-7. doi: 10.1021/ol300913g. Epub 2012 May 21.

Authors

Ji-Qiang Chen¹, Jian-Hua Xie, Deng-Hui Bao, Sheng Liu, Qi-Lin Zhou

Affiliation

¹ State Key Laboratory and Institute of Elemento-organic Chemistry, Nankai University, Tianjin 300071, China.

PMID: 22612349
DOI: 10.1021/ol300913g

Abstract

A synthetic strategy featuring efficient ruthenium-catalyzed asymmetric hydrogenation of racemic α-aryloxy cyclic ketone via dynamic kinetic resolution and palladium-catalyzed intramolecular reductive Heck cyclization has been developed for the asymmetric total synthesis of (-)-galanthamine (20.1%, 12 steps) and (-)-lycoramine (40.2%, 10 steps).

Publication types

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

MeSH terms

Amaryllidaceae Alkaloids / chemical synthesis*
Amaryllidaceae Alkaloids / chemistry
Catalysis
Cyclization
Galantamine / chemical synthesis*
Galantamine / chemistry
Hydrogenation
Molecular Structure
Palladium / chemistry
Ruthenium / chemistry
Stereoisomerism

Substances

Amaryllidaceae Alkaloids
Galantamine
Palladium
Ruthenium
lycoramine