Syntheses of dimeric tetrahydroxanthones with varied linkages: investigation of "shapeshifting" properties
Ransom, Tanya T.
Beutler, John A.
Porco, John A.
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Citation (published version)Tian 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.
The 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.