The creation of multiple stereocenters and their control is important for the synthesis of natural products and pharmaceuticals. The intramolecular Diels-Alder (IMDA) reaction's creation of stereogenic centers has led towards multiple creative total syntheses. However, endo/exo selectivity have not always been straightforward and predictability lacks. More than electronics, sterics, and the particular substituents and configurations of the diene, the conditions for a reaction can dictate the endo/exo selectivity of the reaction. Moreover, some conditions are known to isomerize E,Z dienes to the more stable E,E configuration and again thermodynamics vs. kinetics play significant roles. This study will involve the synthesis of both E,Z and E,E diene appended quinones and quinone derivatives to create tricyclic compounds upon IMDA reactions. These dienes will undergo scrupulous spectroscopic evaluation to determine the endo/exo predictability from each reaction condition.

Investigating endo/exo predictability in the intramolecular Diels-Alder reaction of E,E and E,Z diene appended quinones

2019 Spring National Meeting

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