Concise Total Synthesis of (±)-Aloperine and 6-e pi-Aloperine

D Passarella, M Angoli, A Giardini, G Lesma…

Index: Passarella, Daniele; Angoli, Marco; Giardini, Alessandra; Lesma, Giordano; Silvani, Alessandra; Danieli, Bruno Organic Letters, 2002 , vol. 4, # 17 p. 2925 - 2928

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Citation Number: 14

Abstract

Our retrosynthetic plan (Scheme 1) is based on the key cleavage of the N−C10 bond that reveals the octahydroquinoline system of type A. This moiety is accessible by an intermolecular Diels−Alder reaction of a 5-alkenyl-3,4-dihydropyridin-2-one B with methyl acrylate. We planned to build this N-acylaminodiene 7 by aza-annulation reaction using an acetylenic ketone of type C as a substrate. The presence of the ketone functionality was necessary to induce the ...

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