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Enantiopure N-Boc piperidine-2-ethanol for the synthesis of (+)- and (?)-dumetorine,and (+)- and (?)-epidihydropinidine |
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| Authors: | Daniele Passarella Sergio Riva Gabriele Grieco Francesco Cavallo Begoña Checa Federica Arioli Elena Riva Daniela Comi Bruno Danieli |
| Institution: | 1. Dipartimento di Chimica Organica e Industriale, Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy;2. Istituto di Chimica del Riconoscimento Molecolare, CNR, Via Mario Bianco 9, 20131 Milano, Italy;3. Laboratorio de Quimica Organica, Facultad de Farmacia, Universitad de Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain |
| 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 syntheses are based on a RCM reaction and on methylation of the piperidine ring according to Beak–Lee methodology, respectively. |
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