6. Microwave-Based Reaction Screening: Tandem Retro-Diels–Alder/Diels–Alder Cycloadditions of o-Quinol Dimers
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作者:Suwei Dong, Katharine J. Cahill, Moon-Il Kang, Nancy H. Colburn, Curtis J. Henrich, Jennifer A. Wilson, John A. Beutler, Richard P. Johnson*, and John A. Porco, Jr.*
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发布时间: 2011-11-26
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J. Org. Chem. 2011, 76, 8944-8954.
Suwei Dong, Katharine J. Cahill, Moon-Il Kang, Nancy H. Colburn, Curtis J. Henrich, Jennifer A. Wilson, John A. Beutler, Richard P. Johnson*, and John A. Porco, Jr.*
We have accomplished a parallel screen of cycloaddition partners for O-quinols utilizing a plate-based microwave system. Microwave irradiation improves the efficiency of retro-Diels–Alder/Diels–Alder cascades of O-quinol dimers which generally proceed in a diastereoselective fashion. Computational studies indicate that asynchronous transition states are favored in Diels–Alder cycloadditions of O-quinols. Subsequent biological evaluation of a collection of cycloadducts has identified an inhibitor of activator protein-1 (AP-1), an oncogenic transcription factor.