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

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