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Published on: November 11, 2008
Application of the Solid-Supported Glaser-Hay Reaction to Natural Product Synthesis
Jessica S Lampkowski1, Diya M Uthappa1, John F Halonski1
1Department of Chemistry, College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
Abstract:
The Glaser-Hay coupling of terminal alkynes is a useful synthetic reaction for the preparation of polyynes; however, chemoselectivity issues have precluded its widespread utilization. Conducting the reaction on a solid-support provides a mechanism to alleviate the chemoselectivity issues and provide products in high purities and yields. Moreover, the polyyne core is a key component to several natural products. Herein, we describe the application of a solid-supported Glaser-Hay reaction in the preparation of several natural products. These compounds were then screened for antibacterial activity, illustrating the utility of the methodology.
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