Publication Title

Journal of Undergraduate Chemistry Research

Document Type

Article

Publication Date

Fall 2016

Abstract

Sesquiterpene lactones are plant-derived compounds that have been shown to possess significant activity against inflammation and cancer. Comparative studies of sesquiterpene lactone structure and tumor cytotoxicity indicate that the presence of an α-methylene-γ-lactone moiety is necessary for bioactivity. This observation has led to the hypothesis that simple compounds containing this pharmacophore may also exhibit similar anti-cancer properties. To test this theory, an efficient synthesis of 4-substituted α-methylene-γ-lactone has been developed. The model compound in this study, α-methylene-γ-dodecalactone, has been prepared from commercially available 1-decene in six steps. The synthesis features a nucleophilic epoxide ring-opening reaction followed by an intramolecular cyclization to prepare a key lactone intermediate. The described sequence should provide access to a large number of 4-substituted α-methylene-γ-lactone analogues that can be used to better understand the role alkyl substituents play in the bioactivity of this class of compounds.

Comments

NOTE: This is a PDF of the article as originally published in the Journal of Undergraduate Chemistry Research. It is archived here with the kind permission of the publisher. The original version was published as:

Mechelke, Mark F., Katy Platt, and Connor Pribula (2016). "Chemotherapeutic Drug Design: An Efficient Synthesis of 4-Substituted Alpha-Methylene-Gamma-Lactones." Journal of Undergraduate Chemistry Research, Vol. 15, No. 3.

NOTE: Katy Platt, and Connor Pribula were students enrolled in CHEM 489 - Independent Study and conducted the research for this article under the guidance of Dr. Mark Mechelke.

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