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Ring-expansion Protocol: Preparation Of Synthetically Versatile Dihydrotropones.

Young-Sun Do, Ruiying Sun, H. J. Kim, Jung Eun Yeo, Sung-Hee Bae, S. Koo
Published 2009 · Medicine, Chemistry

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A ring-expansion protocol that consisted of the 1,2-addition of various enolate nucleophiles to 6-trimethylsiloxy-2-cyclohexene-1-one (1) and the NaIO(4)-promoted oxidative ring opening of the resulting diols 2, followed by an intramolecular Knoevenagel condensation, furnished versatile dihydrotropones 6. Maintaining Z-configuration in the oxidative ring-opening products 3 is crucial for the success of the ring-expansion strategy. Dihydrotropones 6 are ripe for further elaborations such as oxidation to tropones 8 and Diels-Alder reaction with the Danishefsky's diene 10 to afford polycyclic compounds 12.

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