Microwave-Based Reaction
Screening: Tandem Retro-Diels–Alder/Diels–Alder
Cycloadditions of <i>o</i>-Quinol Dimers
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Abstract
We have accomplished a parallel screen of cycloaddition
partners
for <i>o</i>-quinols utilizing a plate-based microwave system.
Microwave irradiation improves the efficiency of retro-Diels–Alder/Diels–Alder
cascades of <i>o-</i>quinol dimers which generally proceed
in a diastereoselective fashion. Computational studies indicate that
asynchronous transition states are favored in Diels–Alder cycloadditions
of <i>o</i>-quinols. Subsequent biological evaluation of
a collection of cycloadducts has identified an inhibitor of activator
protein-1 (AP-1), an oncogenic transcription factor