Thursday, 17 May 2007
3rd Floor Hall (Pfahler Hall)
286

Investigation of the Microwave-Assisted Friedel-Crafts Reaction, and it's Application Toward an Improved Total Synthesis of Furoventalene

Melissa Betz Cichowicz, Tristan Colestock, and Tanner Van Dell. West Chester University of Pennsylvania, West Chester, PA

The Friedel-Crafts reaction has received limited attention to date in the field of microwave-assisted organic synthesis. The traditional challenges of low yield and extended reaction times have made development of this reaction in a microwave reactor an attractive goal. A generalized Friedel-Crafts reaction is being examined and optimized for implementation as an undergraduate organic chemistry laboratory exercise, and in addtion, a model system is currently under evaluation to determine the applicability of this method to the total synthesis of furoventalene, a sesquiterpene natural product. A variety of aromatic substrates have been evaluated for the Friedel-Crafts acylation reaction, and one has been chosen for development as an organic laboratory experiment. A model system is currently being optimized for the first step in the furoventalene synthesis, and once the subsequent steps have been carried out, the final coupling step (of an alkenyl side chain with the appropriately functionalized benzofuran) will be evaluated as a candidate for adaptation of a recently described microwave-assisted Kumada coupling reaction.

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