Fluorous and traceless synthesis of substituted indole alkaloids.
The fluorous traceless synthesis of substituted indole alkaloids is carried out first by attaching the 3-(perfluorooctyl)propanol with Boc protected L-tryptophan. The reaction of perfluoroalkyl (Rfh)-tagged tryptophan esters with various aldehydes undergoes Pictet-Spengler reaction to give cis and trans stereoisomers of tetrahydro-beta-carbolines. The nucleophilic addition of the piperidine nitrogen across various isocyanates is followed by the cyclization of ureas and simultaneous rupture of the fluorous tag to afford the hydantoin ring fused tetrahydro-beta-carbolines. All the fluorous-tag compounds are purified by solid-phase extraction (SPE) through Fluoro Flash cartridges.
Lin
Mei-Jung
MJ
Department of Applied Chemistry, National Chiao Tung University, Hsinchu 300, Taiwan.
Zhang
Wei
W
Sun
Chung-Ming
CM
D000433:1-Propanol / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D005466:Fluorocarbons / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry
D005466:Fluorocarbons; D026121:Indole Alkaloids; D014364:Tryptophan; D000433:1-Propanol