Thursday, 17 May 2007 - 11:10 AM
210 (Pfahler Hall)
222

Application of Microwave-Assisted Chemistry to an Improved Total Synthesis of Furoventalene, A Sesquiterpene Natural Product

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

The Friedel-Crafts reaction has received relatively little attention in the field of microwave-assisted organic synthesis. The traditional challenges of low yield and extended reaction time have made the application of microwave technology to this reaction system of interest. Study of the Friedel-Crafts acylation with a variety of aromatic compounds has shown that use of microwaves can give a high yield of the desired product in a short time. One substrate has been chosen to undergo optimization as an experiment in the undergraduate organic laboratory course. In addition, a model system is under evaluation to determine the use of this method toward the total synthesis of furoventalene, which has been synthesized in low yield by a few other research groups.

We have developed a synthetic plan that is more efficient, and further improvement could result if the initial Friedel-Crafts acylation reaction were conducted in the microwave. The final step appears suitable for another microwave-assisted reaction � the Kumada coupling - that has recently been reported in the literature. Other natural product targets will also be identified to which this technology may be applied.


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