- Total syntheses of secalonic acids A and D
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Total syntheses of the dimeric tetrahydroxanthone natural products secalonic acids A and D are described. Key steps involve kinetic resolution of the tetrahydroxanthone core structure using homobenzotetramisole catalysis and late-stage copper(I)-mediated homodimerization of complex aryl stannane monomers. It takes two: Concise syntheses of the natural products secalonic acids A and D using copper(I)-mediated dimerization of complex aryl stannane monomers to construct the requisite 2,2′-biphenol linkage are reported. Highly efficient kinetic resolution of the monomeric tetrahydroxanthone core structures was achieved using homobenzotetramisole catalysis. DMA=N,N-dimethyl acetamide, MOM=methoxymethyl.
- Qin, Tian,Porco Jr., John A.
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- Syntheses of Dimeric Tetrahydroxanthones with Varied Linkages: Investigation of "shapeshifting" Properties
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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.
- Qin, Tian,Iwata, Takayuki,Ransom, Tanya T.,Beutler, John A.,Porco, John A.
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p. 15225 - 15233
(2015/12/18)
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