Canadian journal of chemistry

Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology

GM Strunz, HJ Finlay

Index: Strunz, George M.; Finlay, Heather J. Canadian Journal of Chemistry, 1996 , vol. 74, # 3 p. 419 - 432

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Citation Number: 21

Abstract

The Sakai aryl aldehyde-cyclic ketone aldol-Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substituents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, ...