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

• DOI: 10.1021/acs.joc.6b02407
• Publication Date: 2016-11-30T16:13:45Z
• Authors: Jessica S. Lampko...; Diya M. Uthappa; John F. Halonski; Johnathan C. Maza; Douglas D. Young
• Keywords: Biological Products; Alkynes; Proton Magnetic Resonance Spectroscopy; Carbon-13 Magnetic Resonance Spectroscopy; 01 natural sciences; Catalysis; Mass Spectrometry; 0104 chemical sciences

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.