In parallel with synthetic approaches to both fused and bridged tetracyclic endiandric-type natural products, we have undertaken computational studies to predict the regiochemistry of intramolecular Diels-Alder reactions. Our transition-state calculations have incorporated various substituents and have used both B3LYP and M06-2x functionals. We have also applied density functional theory to examine transition states of several ortho ester Claisen rearrangements that afford diastereomeric products. The computational results from both of these studies allow comparison between experimental and theoretical results to assess the ability of density functional theory to accurately describe these pericyclic transition states.

Computational study of regioselective Diels-Alder and diastereoselective Claisen rearrangement transition states

255th National Meeting (2018)

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