Kava, the Pacific elixir: The asymmetric synthesis of kavain and other pyran-based natural products

ORGN 434

Thomas E. Smith, tsmith@williams.edu, Department of Chemistry, Williams College, Thompson Chemical Laboratory, 47 Lab Campus Drive, Williamstown, MA 01267
New approaches to the asymmetric synthesis of pyran-based natural products will be discussed. The kavalactones, typified by kavain, are a family of about fifteen α,β-unsaturated δ-lactones. These natural products are the biologically active constituents of kava root, which has been used ceremonially in South Pacific cultures for centuries and has attracted recent attention in the Western world as an "alternative" anti-anxiety remedy. Also described will be progress toward the asymmetric total synthesis of the myxobacterial antibiotic, jerangolid D, wherein both the δ-lactone and cis-dihydropyran rings are assembled using an extension of the methods developed for the kavalactones. These methods are further elaborated in their application to the synthesis of the antiviral marine natural product, hennoxazole A.
 

ACS Award for Research at an Undergraduate Institution
8:00 AM-12:00 PM, Wednesday, 29 March 2006 Georgia World Congress Center -- C303/304/305, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006