Application of the Solid-Supported Glaser-Hay Reaction to Natural Product Synthesis.

J Org Chem

Department of Chemistry, College of William & Mary, P.O. Box 8795, Williamsburg, Virginia 23187, United States.

Published: December 2016

AI Article Synopsis

  • * Performing this reaction on a solid support helps overcome these selectivity issues, resulting in higher purity and yield of the desired products.
  • * The study demonstrates the application of this solid-supported method to synthesize natural products, which were then tested for antibacterial properties, showcasing its practical benefits.

Article 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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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC5455993PMC
http://dx.doi.org/10.1021/acs.joc.6b02407DOI Listing

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