Domino Rh-catalyzed hydroformylation-double cyclization of o-amino cinnamyl derivatives: applications to the formal total syntheses of physostigmine and physovenine.
A parallel, versatile and efficient route to synthesis of pyrrolidinoindoline and tetrahydrofuranoindoline alkaloids from cinnamyl derivatives has been developed, featuring a domino Rh-catalyzed hydroformylation-double cyclization sequence. This method can be applied to the syntheses of anti-Alzheimer drugs such as physostigmine and physovenine.
Department of Chemistry, National Chung Hsing University, Taichung, 402, Taiwan, ROC. wchiou@dragon.nchu.edu.tw
Wen-Hua
WH
Chiou
Chien-Lun
CL
Kao
Jui-Chi
JC
Tsai
Yun-Man
YM
Chang
D002384:Catalysis; D002934:Cinnamates / Q000737:chemistry*; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D010830:Physostigmine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
D002934:Cinnamates; C092643:physovenine; D010830:Physostigmine; D012238:Rhodium