A cycloaddition strategy for use toward Berkelic acid, an MMP inhibitor and potent anticancer agent displaying a unique chroman spiroketal motif
A kinetically controlled diastereoselective cycloaddition between a chiral enol ether and an ortho-quinone methide (o-QM) produces a chroman spiroketal motif that is found in the core of berkelic acid, a novel matrix metalloproteinase (MMP) inhibitor and potent anticancer agent. The transformation lays the groundwork for preparation of future inhibitors aimed at distinguishing among the active sites of the twenty-three known MMP. Experimental findings suggest that the stereochemistry that emerges from cycloaddition is opposite that which results from thermodynamic ketalization. Georg Thieme Verlag Stuttgart.
Diastereoselective syntheses of chroman spiroketals via [4 + 2] cycloaddition of enol ethers and o-quinone methides
(Chemical Equation Presented) A variety of chroman spiroketals are synthesized via inverse-demand [4 + 2] cycloaddition of enol ethers and ortho-quinone methides (o-QMs). Low temperature o-QM generation in situ allows for the kinetic, diastereoselective construction of these motifs, providing entry to a number of unusual chroman spiroketal natural products.
Marsini, Maurice A.,Huang, Yaodong,Lindsey, Christopher C.,Wu, Kun-Liang,Pettus, Thomas R. R.
supporting information; experimental part
p. 1477 - 1480
(2009/04/10)
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