Chiral total synthesis of (+)-montbretyl 12-methyl ether and (-)-montbretyl 12-methyl ether

Authors
Li, AP Peng, XS Wu, XM Wu, TX Pan, XF
Citation
Ap. Li et al., Chiral total synthesis of (+)-montbretyl 12-methyl ether and (-)-montbretyl 12-methyl ether, CHEM J CH U, 22(9), 2001, pp. 1511-1514
Citations number
11
Categorie Soggetti
Chemistry
Journal title
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE
ISSN journal
02510790 → ACNP
Volume
22
Issue
9
Year of publication
2001
Pages
1511 - 1514
Database
ISI
SICI code
0251-0790(200109)22:9<1511:CTSO(1>2.0.ZU;2-A
Abstract
By using (S)-(-)-alpha -cyclocitral(9a) and (R)-(+)-alpha -cyclocitral(9b) obtained by chemical resolution as the A ring synthon, and triphenyl phosph onium chloride (18) obtained from p-bromoanisole via eight steps as the C r ing synthon, the sole trans key intermediate 3 was obtained after the conde nsation and intracyclization reactions. The structure modification, (+)-mon tbretyl 12-methyl ether (1a) and (-)-montbretyl 12-methyl ether(1b) were ob tained enantioselectively. The cyclization reaction of BF3 . Et2O is the ke y step.