We report a Bronsted acid-catalyzed carbocation mediated carbocylization reaction leading to densely functionalized tetrahydrofluorene tricyclic core structures. This transformation of electron rich, poor and neutral aryl ketones has enabled synthetic access to tricyclic core structures incorporated in many biologically active target structures. This method represents an alternative to currently available reaction protocols relying on stoichiometric reagents and high-energy allene-yne precursors. Mechanistic studies are described that have led to the development of a carbocation trapping mechanistic hypothesis that is supported by the isolation and characterization of distinct intermediates.

Development of an interrupted carbonyl-olefin metathesis reaction

253rd National Meeting (2017)

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