Electrocyclic Reactions in Organic Synthesis

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The Synthetic Organic Program will support the research of Dr. Peter A. Jacobi of the Department of Chemistry at Wesleyan University by means of an Accomplishment Based Renewal award. He will continue to develop methodology that leads to the preparation of ring-containing organic molecules. The specific process, known as bis-heteroannulation, affords fused-ring furans, prepared with complete regiochemical control. The key element in Dr. Jacobi's approach involves the intramolecular Diels-Alder reaction between an oxazole and an acetylene. In addition to the bis-heteroannulation work, tandem sigmatropic rearrangements will be used for the tranformation of acetylenic alcohols or enones into methylenecyclopentanones or phenols. Syntheses of a number of naturally occuring phenols and sesquiterpenes will illustrate the usefulness of the methodology.