Formal total synthesis of (-)-emetine using catalytic asymmetric allylation of cyclic imines as a key step.
[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.
Itoh
Takashi
T
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan. itoh-t@pharm.showa-u.ac.jp
Miyazaki
Michiko
M
Fukuoka
Hiromi
H
Nagata
Kazuhiro
K
Ohsawa
Akio
A
D002384:Catalysis; D003500:Cyclization; D004640:Emetine / Q000138:chemical synthesis* / Q000737:chemistry; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D007097:Imines; D004640:Emetine