Endiandric acids and related natural products are biosynthesized from polyene precursors into fused or bridged tetracycles, via either of two Diels-Alder reactions. To test what factors affect the preference for fused or bridged products, density functional theory was applied to the Diels-Alder precursors and transition states. Various substituents were tested and compared using the M06-2X functional. Steric and electronic effects of substituents and catalysts on the fused vs. bridged product ratio will be presented. These computational results will also be compared to experimental Diels-Alder results.

Computational comparisons of Diels-Alder transition states for endiandric tetracycles using density functional theory

253rd National Meeting (2017)

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