Synthesis of 2-oxo-16-(3', 4'-methylenedioxyphenyl)-trans-15-hexadecene

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.

Brody, Judy, interviewed by Jena Hershkowitz on January 19, 2010: Audio Recording

Some themes discussed are: • Jewish education—Hebrew tutor/Hebrew school(1) • Jewish education—Sunday School(10) • Jewish education—parents (12) • Holidays (1-2) • Civic engagement (1, 5) • Civic engagement—B’nai B’rith and Hadassah (2) • Food—kosher (2) • Colby—Greek life (3-4) • Occupation—law (4) • Dating—marriage (5) • Dating—at Colby (8) • Dating—interfaith marriage (9) • Live in Waterville—attractions (6) • Live in Waterville—school (9) • Colby—Hillel (6) • Colby—classes (6) • Colby—campus life (7-8, 12-13) • Synagogue (11)