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Ruthenium-catalyzed insertion of adjacent diol carbon atoms into C-C bonds: Entry to type II polyketides

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Science  25 Aug 2017:
Vol. 357, Issue 6353, pp. 779-781
DOI: 10.1126/science.aao0453

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Slicing through both C-C and C-H bonds

A variety of catalysts can cleave the strained bonds in four-membered carbon rings and then link the ends to a reactive partner. Bender et al. found that after prying the ring open, a double-duty ruthenium catalyst could forge bonds to a traditionally unreactive partner. They used the reaction to couple cyclobutenones to adjacent saturated carbon centers in diols. This approach efficiently yielded a motif common in polyketide natural products. The reaction proceeds through dehydrogenation and is also amenable to coupling the opened rings to ketol or dione reagents.

Science, this issue p. 779

Abstract

Current catalytic processes involving carbon-carbon bond activation rely on π-unsaturated coupling partners. Exploiting the concept of transfer hydrogenative coupling, we report a ruthenium(0)-catalyzed cycloaddition of benzocyclobutenones that functionalizes two adjacent saturated diol carbon-hydrogen bonds. These regio- and diastereoselective processes enable convergent construction of type II polyketide substructures.

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