title: Application of the Solid-Supported Glaser-Hay Reaction to Natural Product Synthesis.
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.
authors.affiliation: Department of Chemistry, College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
authors.forename: Jessica S
authors.initials: JS
authors.lastname: Lampkowski
authors.affiliation: Department of Chemistry, College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
authors.forename: Diya M
authors.initials: DM
authors.lastname: Uthappa
authors.affiliation: Department of Chemistry, College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
authors.forename: John F
authors.initials: JF
authors.lastname: Halonski
authors.affiliation: Department of Chemistry, College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
authors.forename: Johnathan C
authors.initials: JC
authors.lastname: Maza
authors.affiliation: Department of Chemistry, College of William & Mary , P.O. Box 8795, Williamsburg, Virginia 23187, United States.
authors.forename: Douglas D
authors.identifier: 0000-0003-4433-4101
authors.initials: DD
authors.lastname: Young
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002384:Catalysis; D013058:Mass Spectrometry; D066244:Proton Magnetic Resonance Spectroscopy
chemical_list: D000480:Alkynes; D001688:Biological Products