Synthesis of sedamine by tethered cyclofunctionalisation.
The piperidine alkaloid, (+)-sedamine has been synthesised starting from (S)-1-phenyl-3-butenol using a stereoselective, intramolecular palladium-catalysed cyclocarbonylation reaction of a substituted hydroxylamine.
Bates
Roderick W
RW
Department of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, UK. R.W.Bates@exeter.ac.uk
Boonsombat
Jutatip
J
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D000440:Butanols / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D003500:Cyclization; D008968:Molecular Conformation; D010165:Palladium / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C511277:(S)-1-phenyl-3-butenol; D000470:Alkaloids; D000440:Butanols; D010880:Piperidines; C459239:sedamine; D010165:Palladium; D003300:Copper