Total synthesis of (-)-isoschizogamine.
A first asymmetric total synthesis of (-)-isoschizogamine has been accomplished. Our synthesis features the facile construction of the carbon framework of the natural product through a Wagner-Meerwein rearrangement, a tandem metathesis, a stereoselective rhodium-mediated 1,4-addition of an arylboronic acid, and a ring-closing metathesis via a hemiaminal ether.
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Yusuke
Y
Miura
Noriyuki
N
Hayashi
Satoshi
S
Yokoshima
Tohru
T
Fukuyama
D000470:Alkaloids / Q000138:chemical synthesis*; D029062:Apocynaceae / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D001897:Boronic Acids / Q000737:chemistry; D003500:Cyclization; D026121:Indole Alkaloids; D007211:Indoles / Q000138:chemical synthesis*; D012238:Rhodium / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001688:Biological Products; D001897:Boronic Acids; D026121:Indole Alkaloids; D007211:Indoles; C409122:isoschizogamine; D012238:Rhodium