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a A convergent and modular synthesis of dienyl and diynyl isobutylamide natural products from echinacea and spilanthes herbal medicines

UNCG Author/Contributor (non-UNCG co-authors, if there are any, appear on document)
Gabriel A. Miller (Creator)
Institution
The University of North Carolina at Greensboro (UNCG )
Web Site: http://library.uncg.edu/
Advisor
Jason Reddick

Abstract: ""Echinacea" and "Spilanthes" are popular over-the-counter herbal supplements derived from raw tissue or tissue extracts from plants such as Echinacea purpurea and Spilanthes acmella, respectively. Several chemical constituents have been identified as possible candidates for these plants' supposed medicinal activities, and include the "alkylamides," of which dienyl and diynyl analogs are prominent members. Isolation of these compounds from the plants is often difficult and results in poor yields. The goal of our research was to develop an encompassing synthesis scheme for dienyl and diynyl alkylamides (Figure 1) addressing consistent functional groups, using a Wittig reaction, a Horner-Wadsworth-Emmons reaction and a Sonogashira reaction. The total syntheses for these compounds are not novel, but have been known to be rather lengthy procedures. We are pleased to offer a novel synthesis that can synthesize a derivative of Spilanthol which involves only three reactions and well developed method for the diynyl structures using the Sonogashira coupling reaction."--Abstract from author supplied metadata.

Additional Information

Publication
Thesis
Language: English
Date: 2007
Keywords
Echinacea, Spilanthes, over the counter, herbal, supplements, Echinacea purpurea, Spilanthes acmella, chemical, medicinal, alkylamides
Subjects
Echinacea (Plants)
Spilanthes
Botanical chemistry