Synthesis of Alkaloids of Galipea officinalis by Alkylation of an α??Amino Nitrile

…, JL Renaud, P van de Weghe, T Roisnel

Index: Shahane, Saurabh; Louafi, Fadila; Moreau, Julie; Hurvois, Jean-Pierre; Renaud, Jean-Luc; Van De Weghe, Pierre; Roisnel, Thierry European Journal of Organic Chemistry, 2008 , # 27 p. 4622 - 4631

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Citation Number: 22

Abstract

Abstract A new synthetic approach directed towards the synthesis of naturally occurring 2- alkyl-tetrahydroquinolines is described. The C–C bonds in the α position relative to the nitrogen atom were formed by the reversal of the polarity of the C= N bond of α-amino nitrile 6, which was prepared electrochemically from 1-(phenylethyl)-tetrahydroquinoline. A NaBH 4-mediated reductive decyanation process furnished benzylic amines 16a–d as mixtures ...