Reactivity of cyclohexene epoxides toward intramolecular acid-catalyzed cyclizations for the synthesis of naturally occurring cage architectures |
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Authors: | Hajer Abdelkafi Laurent Evanno Alexandre Deville Lionel Dubost Bastien Nay |
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Institution: | Muséum national d’Histoire naturelle, unité molécules de communication et adaptation des micro-organismes (UMR 7245 CNRS-MNHN), 57, rue Cuvier (CP 54), 75005 Paris, France |
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Abstract: | This account compiles our results on the reactivity of cyclohexene epoxides toward the synthesis of naturally occurring cage architectures, in particular, the one found in harringtonolide. Bicyclic and branched monocyclic functional triads (hydroxy-epoxy-esters) were synthesized with the aim of undertaking cascade processes toward the formation of lactone and/or cycloether bridges, through a central epoxide opening. This work successfully culminated in the cascade cyclization of the fully oxygenated bridge-structure of harringtonolide, by using a dual Brønsted-Lewis acid complex. |
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