Endiandric acids and related natural products arise from polyene precursors and occur naturally as fused and bridged tetracycles. Both types of tetracycles are formed in an intramolecular Diels-Alder reaction in which an unsaturated tether could act as a diene (leading to a fused product) or a dienophile (leading to a bridged product). To test what factors affect the preference for fused or bridged products, density functional theory (using the M06-2X and B3LYP functionals) was applied to reactants with varied substituents for both fused and bridged transition states. Steric and electronic effects on selectivities for fused or bridged products will be presented. These computational results are guiding our synthetic work towards fused and bridged tetracycles.

Computational comparisons of intramolecular Diels-Alder transition states leading to fused and bridged tetracycles

251st National Meeting (2016)

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