Synthesis of the ABC ring system of manzamine A

I Coldham, KM Crapnell, JC Fernàndez…

Index: Coldham, Iain; Crapnell, Katherine M; Fernandez, Joan-Carles; Moseley, Jonathan D; Rabot, Remi The Journal of organic chemistry, 2002 , vol. 67, # 17 p. 6181 - 6187

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Citation Number: 50

Abstract

A synthesis of the core ABC ring system of the manzamine alkaloids is described, starting from arecoline. The key steps involve a Claisen rearrangement to set up a 4-substituted-3- methylenepiperidine and a stereoselective azomethine ylide dipolar cycloaddition reaction. Condensation of the aldehyde 6 and sarcosine ethyl ester hydrochloride salt gives an intermediate azomethine ylide, which undergoes an intramolecular cycloaddition reaction ...