The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The synthesis are based on RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively
Enantiopure N-Boc Piperidine-2-ethanol for the Synthesis of(+)- and (-)-Dumetorine and (+)- and (-)-Epidihydropinidine / D. Passarella, S. Riva, G. Grieco, F. Cavallo, B. Checa, F. Arioli, E. Riva, D. Comi, B. Danieli. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 20:2(2009 Jan), pp. 192-197. [10.1016/j.tetasy.2008.12.008]
Enantiopure N-Boc Piperidine-2-ethanol for the Synthesis of(+)- and (-)-Dumetorine and (+)- and (-)-Epidihydropinidine
D. Passarella;E. Riva;D. Comi;B. Danieli
2009
Abstract
The convenient synthesis of both enantiomers of the piperidine alkaloids such as dumetorine and epidihydropinidine is described. Pure enantiomers of 2-(2-hydroxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester are used as a common starting material. The synthesis are based on RCM reaction and on methylation of the piperidine ring according to Beak-Lee methodology, respectively
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