1019848-76-0Relevant articles and documents
A cycloaddition strategy for use toward Berkelic acid, an MMP inhibitor and potent anticancer agent displaying a unique chroman spiroketal motif
Huang, Yaodong,Pettus, Thomas R. R.
, p. 1353 - 1356 (2008)
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.
