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Publication Title

Journal of Undergraduate Chemistry Research

Document Type

Peer Reviewed Article

Publication Date



Goniothalamin, a natural product isolated from the dried stem bark of Malaysian plants of the genus Goniothalamus, has been shown to induce apoptosis in cancer cells. The bioactivity of this molecule is though to be due to its ability to react with thiols. One mechanism involves its reaction with glutathione, a natural antioxidant found in all cells. Using a four step synthetic sequence, a novel gamma-lactone analogue of goniothalamin has been prepared that replaces the endocylic double bond in goniothalamin's lactone core with an exocyclic double bond. It is anticipated that this alteration will allow the compound to react more rapidly with thiols and therefore increase its cytotoxicity towards cancer cells.


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., et al. (2014). "Design and Synthesis of a Novel Alpha-Methylene Lactone Chemotherpeutic Agent." Journal of Undergraduate Chemistry Research, Vol. 13, No. 1. Available to subscribers at

NOTE: All of the student authors were enrolled in CHEM 489 - Independent Study and conducted the research for this article under the guidance of Dr. Mark Mechelke.

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Chemistry Commons



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