Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 137, Issue 18, Pages 5883-5886Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.5b02755
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Funding
- Robert A. Welch Foundation [F-0038]
- NIH-NIGMS [R01-GM093905]
- Center for Green Chemistry and Catalysis
- Rusan Pharma Ltd.
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Upon exposure of 3,4-benzannulated 1,5-diynes (benzo-endiynes) to alpha-ketols (alpha-hydroxyketones) in the presence of Ru(0) catalysts derived from Ru-3(CO)(12) and RuPhos or CyJohnPhos, successive redox-triggered C-C coupling occurs to generate products of [4 + 2] cycloaddition. The proposed catalytic mechanism involves consecutive alkyne-carbonyl oxidative couplings to form transient oxaruthanacycles that suffer alpha-ketol mediated transfer hydrogenolysis. This process provides a new, convergent means of assembling Type II polyketide substructures.
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