(±)-1α-Nitro-2β-[3-(6-chloropyridyl)]-cyclohexanone, a key intermediate for a stereocontrolled synthesis of the alkaloid epibatidine, possessing a 7-azanorbornane structure to which is attached, in an exo-orientation, a 5-(2-chloropyridyl) substituent, has been prepared either by Diels-Alder reaction or tandem Michael reaction by way of 5-(2-nitrovinyl)-2-chloropyridine as common starting material and 2-trimethylsilyloxy-1,3-butadiene or methyl 3-oxo-4-pentenoate as counterparts respectively.
Total synthesis of (+/-)-epibatidine
BARCO, Achille;BENETTI, Simonetta;DE RISI, Carmela;POLLINI, Gian Piero;ROMAGNOLI, Romeo;ZANIRATO, Vinicio
1994
Abstract
(±)-1α-Nitro-2β-[3-(6-chloropyridyl)]-cyclohexanone, a key intermediate for a stereocontrolled synthesis of the alkaloid epibatidine, possessing a 7-azanorbornane structure to which is attached, in an exo-orientation, a 5-(2-chloropyridyl) substituent, has been prepared either by Diels-Alder reaction or tandem Michael reaction by way of 5-(2-nitrovinyl)-2-chloropyridine as common starting material and 2-trimethylsilyloxy-1,3-butadiene or methyl 3-oxo-4-pentenoate as counterparts respectively.File in questo prodotto:
Non ci sono file associati a questo prodotto.
I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
