Numerous biologically and chemically relevant natural products possess the chromanone or flavanone core structure. We will describe our efforts toward the development of an approach to the synthesis of chromanones and flavanones using C-H bond functionalization. It has been well established that benzyl and allyl ethers undergo oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to produce oxonium ions that can be trapped with pendent nucleophiles to produce a oxygen heterocycles. We have prepared several substrates possessing allyl and benzyl ether pro-electrophilic sites and enol acetate, silyl enol ether and β-dicarbonyl nucleophilic sites that would produce chromanones or flavonanones upon successful oxidative cyclization and examined their reactivity with DDQ. The results of these studies, which indicate that the presence of the requisite phenyl allyl or phenyl benzyl ether prevents the expected reactivity, will be presented.

C-H bond functionalization approach to chromanones

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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