Date of Award
2006
Document Type
Honors Thesis (Open Access)
Department
Colby College. Chemistry Dept.
Advisor(s)
Dasan M. Thamattoor
Second Advisor
Thomas Shattuck
Abstract
This work presents the progress made towards synthesizing 2-oxo-16-(3', 4'methylenedioxyphenyl)-trans-15-hexadecene, an antimycobacterial compound that was originally isolated from the leaves of Piper Sanctum. The hydrocarbon chain of the molecule was synthesized first by opening a 15-pentadecanolactone ring by means of HI, and performing an E2 elimination reaction on the molecule followed by an organolithium reaction with CH3Li. Hexadec-15-en-2-one that was afforded this way was later reacted with 5-bromobenzo[d][1,3]dioxole following the appropriate Heck reaction protocol that allows for the formation of a palladium catalyzed carbon-carbon bond.
The modes of action of 2-oxo-16-(3', 4'-methylenedioxyphenyl)-trans-15hexadecene are comparable to the ones of rifampicin, a marketable drug that has been successfully used in the treatment of tuberculosis in the past. Additionally, this compound can serve as an intermediate towards the synthesis of 2-oxo-16-(3', 4' methylenedioxyphenyl)-hexadecane and 2-oxo-14-(3', 4' -methylenedioxyphenyl) tetradecane, both strong inhibitors of the growth of Mycobacterium tuberculosis. Lastly, due to Multi-Drug Resistant tuberculosis, there has been an increasing need to find alternative cures for tuberculosis. Therefore, the work on 2-qxo-16-(3', 4'methylenedioxyphenyl)-trans-15-hexadecene is not only chemically interesting but it is also biologically important.
Keywords
Mycobacterium tuberculosis, hydrocarbon, Multi-Drug Resistant, tuberculosis
Recommended Citation
Zorba, Adelajda, "Synthesis of 2-oxo-16-(3', 4'-methylenedioxyphenyl)-trans-15-hexadecene" (2006). Honors Theses. Paper 486.https://digitalcommons.colby.edu/honorstheses/486
Copyright
Colby College theses are protected by copyright. They may be viewed or downloaded from this site for the purposes of research and scholarship. Reproduction or distribution for commercial purposes is prohibited without written permission of the author.