Enantioselective allyltitanations and metathesis reactions. Application to the synthesis of piperidine alkaloids (+)-sedamine and (-)-prosophylline.
An enantioselective synthesis of the piperidine alkaloids (+)-sedamine and (-)-prosophylline is reported. The synthesis of (+)-sedamine has been achieved in 12 steps with an overall yield of 20% from benzaldehyde, and (-)-prosophylline was obtained in 15 steps with an overall yield of 9.2%, starting from D-glyceraldehyde acetonide 14. The key steps are enantioselective allyltitanation reactions and ring-closing or cross-metathesis reactions.
Cossy
Janine
J
Laboratoire de Chimie Organique associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France. janine.cossy@espci.fr
Willis
Catherine
C
Bellosta
Véronique
V
BouzBouz
Samir
S
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001547:Benzaldehydes / Q000737:chemistry; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D004988:Ethers, Cyclic / Q000737:chemistry; D005985:Glyceraldehyde / Q000031:analogs & derivatives / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D001547:Benzaldehydes; D004988:Ethers, Cyclic; D010880:Piperidines; C459241:glyceraldehyde acetonide; C459240:prosophylline; C459239:sedamine; D005985:Glyceraldehyde; C032175:benzaldehyde