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Stable 5-Substituted Cyclopentadienes for the Diels–Alder Cycloaddition and their Application to the Synthesis of Palau'amine

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  • This work was supported by the NSERC. J.H. thanks the NSERC and the FQRNT for predoctoral fellowships. T.A.C. thanks the FQRNT for a predoctoral fellowship. J.A.A. thanks the Walter C. Sumner Foundation for a predoctoral fellowship.

Abstract

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Putting the brakes on a hydride shift: The incorporation of a 2-silyloxy group increases both the stability and reactivity of 5-substituted cyclopentadienes, thus facilitating their preparation and use (see scheme; Bz=benzyl, TBS=tert-butyldimethylsilyl). This approach has been applied to the synthesis of the E ring in the marine alkaloid palau'amine.

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