4’ -ester analogues of resveratrol were synthesized using reaction conditions developed to produce mono-ester products in the presence of two other unprotected phenols. Basic conditions were employed to deprotonate the most acidic 4’ phenol followed by addition of anhydrides or acid chlorides to give the ester product. The reaction favored 4’-ester formation in polar aprotic solvents with DMSO being the optimal solvent.
(—)-Englerin A is a guaiane-type sesquiterpene containing two ester side chains. Mimics of (—)-englerin A were proposed that retained the ester side chains while replacing the non-polar core with less complicated structures. These proposed mimic cores would maintain the three-dimensional positioning of the esters which are responsible for the anti-cancer activity of (—)-englerin A. Three mimics were synthesized using the bicyclic terpenes borneol and fenchol. Installation of the second ester on the terpene core was accomplished throught the development and optimization of a unique methylene oxidation using chromium trioxide in glacial acetic acid. These mimics were screened against two kidney cancer cell lines. The compounds were shown to have IC50 (inhibitory concentration for 50 % of cells) values above 30 µM.
College and Department
Physical and Mathematical Sciences; Chemistry and Biochemistry
BYU ScholarsArchive Citation
Acerson, Mark Jeffrey, "Synthesis of 4'-Ester Resveratrol Analogues, Chromium Trioxide Oxidation of Terpenes, and Synthesis of Mimics of (-)-Englerin A" (2014). All Theses and Dissertations. 5458.
resveratrol, englerin A, Analogue, Mimic, polyphenol, anti-viral, anti-cancer, methylene oxidation, selective esterification