Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step

Takashi Itoh; Michiko Miyazaki; Hiromi Fukuoka; Kazuhiro Nagata; Akio Ohsawa

doi:10.1021/ol0530326

Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step

Org Lett. 2006 Mar 30;8(7):1295-7. doi: 10.1021/ol0530326.

Authors

Takashi Itoh¹, Michiko Miyazaki, Hiromi Fukuoka, Kazuhiro Nagata, Akio Ohsawa

Affiliation

¹ School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. [email protected]

PMID: 16562875
DOI: 10.1021/ol0530326

Abstract

[reaction: see text] Catalytic asymmetric allylation of 3,4-dihydro-6,7-dimethoxyisoquinoline was carried out using allyltrimethoxysilane in the presence of Cu(I) and tol-BINAP. The allyl adduct thus obtained was transformed to a chiral synthetic intermediate for (-)-emetine in good yield. The procedure was applied to the total synthesis of ent-emetine.

MeSH terms

Catalysis
Cyclization
Emetine / chemical synthesis*
Emetine / chemistry
Imines / chemistry*
Molecular Structure
Stereoisomerism

Substances

Imines
Emetine