Qin, TianIwata, TakayukiRansom, Tanya T.Beutler, John A.Porco, John A.2018-01-302018-01-302015-12-09Tian Qin, Takayuki Iwata, Tanya T Ransom, John A Beutler, John A Porco. 2015. "Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "Shapeshifting" Properties.." J Am Chem Soc, Volume 137, Issue 48, pp. 15225 - 15233.1520-5126https://hdl.handle.net/2144/26491The 2,4'- and 4,4'-linked variants of the cytotoxic agent secalonic acid A and their analogues have been synthesized. Kinetic resolution of an unprotected tetrahydroxanthone scaffold followed by copper-mediated biaryl coupling allowed for efficient access to these compounds. Evaluation of the "shapeshifting" properties of 2,2'-, 2,4'-, and 4,4'-linked variants of the secalonic acids A in a polar solvent in conjunction with assays of the compounds against select cancer cell lines was conducted to study possible correlations between linkage variation and cytotoxicity.p. 15225 - 15233Science & technologyPhysical sciencesChemistryEnantioselective total synthesisPhomopsis longicollaBlennolide CMonomeric chromanonesMichael additionSecalonic acidXanthone dimersGonytrichum sp.Cell line, tumorDimerizationHumansKineticsXanthonesChemical sciencesGeneral chemistryArticle10.1021/jacs.5b09825