Studies directed toward the synthesis of the hyperforin class of natural products based on an intramolecular allene-nitrile oxide cycloaddition will be described. Isoxazoline 2 is envisioned to be a viable intermediate in a synthetic approach to 1 and other family members, and progress toward the synthesis of 2 starting from appropriate vinylogous esters 4 will be presented. Thus the stereocontrolled synthesis of vinylogous esters 4, their conversion to fully prenylated ƒÑ-allenyl ketones 3 and stereoselective introduction of an A-ring surrogate will be described.
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