Thursday, 3 November 2005 - 8:30 AM

This presentation is part of: Organic Chemistry - General Papers III

Hyperforin Synthetic Studies

David G.J. Young, Joseph A. Burlison, and Dongxiang Zeng.

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 -allenyl ketones 3 and stereoselective introduction of an A-ring surrogate will be described.

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