A highly concise one-pot method towards biologically relevant compounds having a [6-5-6]- and [5-5-6]-tricyclic framework has been established. Specifically, we have developed a tandem Diels-Alder/Nazarov cyclization of ß-silyl substituted aryl ynones to generate carbo- and heterocyclic fused ring systems in good to excellent yields. This method generates three new carbon-carbon bonds, a quaternary carbon, and two stereogenic centers with excellent diastereo- and regiocontrol, under mild Lewis acidic conditions. Stabilization of the oxyallyl cation intermediate via the ß-silyl effect is key to the success of this reaction.

Tandem diels-alder/Nazarov cyclization of ß-silyl-substituted aryl ynones

253rd National Meeting (2017)

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