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À propos de : A Stereoselective Synthesis of (±)-C-Secolimonoid BCDE ModelCompounds Related to the Insect Antifeedant Ohchinolide        

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  • A Stereoselective Synthesis of (±)-C-Secolimonoid BCDE ModelCompounds Related to the Insect Antifeedant Ohchinolide
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  • A short and stereoselective synthesis of a (±)-BCDE C-secolimonid model insect antifeedant relatedto ohchinolide and nimbolidin was accomplished in 13 (30% overall yield) and 15 (30% overall yield)steps, respectively, from ethyl drimanate. The key steps are the torquoselective electrocyclizationof the divinyl ketone 6, induced by perchloric acid, and the stereoselective rearrangement of thehydroxy lactone 12, inspired in a biosynthetic proposal. An alternative route, which provides accessto (±)-BCDE ohchinolide and nimbolidin isomers, is also described.
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