Synthesis of Active Antifeedant CDE Fragments of 11-Ketoepoxyazadiradione Based on an Electrocyclization Reaction Catalyzed by Perchloric Acid
The Journal of Organic Chemistry1998Vol. 63(25), pp. 9440–9447
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A. Fernández‐Mateos, E.M.M. De La Nava, Gustavo Pascual Coca, R. Rubio González, Ana I. Ramos Silvo, Monique S. J. Simmonds, W. M. Blaney
Abstract
A synthetic route to mimics of the insect antifeedant epoxyazadiradione containing the CDE molecular fragment with an oxygenated function on ring C has been developed. The key step is based on a 2,6-diene-1,5-dione electrocyclization reaction catalyzed by perchloric acid. The rearrangement of the epoxy alcohol epimers 12 and 19 induced by acids deserves special mention. Several of the compounds obtained show significant antifeedant activity against Spodoptera frugiperda.
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