Diels-Alder [4+2] cycloadditions are among the most common of all organic reactions, however far less recognized are [5+2] cycloadditions. Bridged polycyclic ethers produced from oxidopyrylium-alkene [5+2] cycloadditions are found in a plethora of diverse biologically active natural products. Investigating the functionality of these structures will allow for discovery of regio-, chemo-, and stereoselective transformations.<br/>In a model system, we focus on the four step synthesis of a pyrone to be used as the starting material for asymmetric [5+2] cycloadditions. As we continue our investigation, we focus on pathways toward diastereo- and enantioselectivity. Toward that end, both chiral auxiliaries and catalysts will be utilized in order to synthesize heterocyclic scaffolds useful for the synthesis of natural and unnatural products.

Investigation of [5+2] cycloadditions

251st National Meeting (2016)

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