Tetrahedron

A brief and stereoselective synthesis of limonoid models, with antifeedant activity against Locusts migratoria

A Fernández-Mateos, AIR Silvo, RR González…

Index: Fernandez-Mateos; Ramos Silvo; Rubio Gonzalez; Simmonds Tetrahedron, 2006 , vol. 62, # 33 p. 7809 - 7816

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Citation Number: 14

Abstract

A short stereoselective preparation of havanensin-type limonoid models is reported. The synthesis is based on a radical domino reaction of an epoxyketone to a bicyclic hydroxyketone, and is achieved in six and nine steps from simple cyclohexenones. The epoxyhavanensin derivatives show significant antifeedant activity against Spodoptera littoralis and Spodoptera frugiperda, and the epoxyketone 21 shows potent antifeedant ...