Resveratrol-derived natural products are known to have useful antibiotic and antifungal properties. Synthetic efforts towards these compounds have largely been limited to enzymatic transformations and racemic syntheses. To remedy the absence of enantioselective synthetic techniques, we recently developed a methodology that efficiently assembles the benzodihydrofuran core embedded in many resveratrol derivatives. Our one-pot method oxidizes a hydrazone to a diazo intermediate, which then undergoes Rh-catalyzed C-H insertion. In 2014, we applied our methodology toward the first asymmetric synthesis of the resveratrol derivative <i>E</i>-δ-viniferin. Current efforts aimed at assembling more complex resveratrol-derived natural products are described.

Enantioselective C-H insertions for the synthesis of complex natural products

251st National Meeting (2016)

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