The goal of this research is to further develop oxidopyrylium-alkene [5+2] cycloadditions as a synthetic tool toward bridged polycyclic ethers that are common in diverse biologically active natural products. Previous literature reports of intramolecular oxidopyrylium-alkene [5+2] cycloadditions with α-silyloxypyrones suggest a hypothesis of silyl transfer as the rate-determining step. Currently, various α-silyloxypyrones are being utilized to investigate the nature of the silyl transfer in [5+2] cycloadditions. Various protecting groups and alkenes tethered to the α-silyloxypyrone have provided mechanistic insights based on proposed electronic perturbations effecting conversion rates. As the electronic parameters of intramolecular variants are probed, this could provide insight toward more selective intermolecular [5+2] cycloadditions.

Investigation of clectronic variables of x-pyrone-based oxidopyrylium-alkene [5+2] cycloadditions

255th National Meeting (2018)

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