Asymmetric synthesis of (+)-castanospermine through enol ether metathesis-hydroboration/oxidation.
An asymmetric synthesis of (+)-castanospermine is presented in which enol ether metathesis-hydroboration/oxidation is used for stereoselective installation of the trans-trans hydroxyl groups on the piperidine ring of the alkaloid.
Université Joseph Fourier, Département de Chimie Moléculaire (SERCO) UMR-5250, ICMG FR-2607, CNRS, BP 53, 38041, Grenoble Cedex 9, France.
Julien
J
Ceccon
Grégory
G
Danoun
Andrew E
AE
Greene
Jean-François
JF
Poisson
D000470:Alkaloids / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004986:Ether / Q000737:chemistry; D004987:Ethers / Q000737:chemistry*; D007212:Indolizines / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010880:Piperidines / Q000737:chemistry*; D013237:Stereoisomerism; D054836:Indolizidines
D000470:Alkaloids; D004986:Ether; D004987:Ethers; D007212:Indolizines; D010880:Piperidines; C032727:piperidine; C037806:castanospermine; D054836:Indolizidines