title: Microwave-based reaction screening: tandem retro-Diels-Alder/Diels-Alder cycloadditions of o-quinol dimers.
abstract: 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.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, Boston, Massachusetts 02215, United States.
authors.forename: Suwei
authors.initials: S
authors.lastname: Dong
authors.forename: Katharine J
authors.initials: KJ
authors.lastname: Cahill
authors.forename: Moon-Il
authors.initials: MI
authors.lastname: Kang
authors.forename: Nancy H
authors.initials: NH
authors.lastname: Colburn
authors.forename: Curtis J
authors.initials: CJ
authors.lastname: Henrich
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Wilson
authors.forename: John A
authors.initials: JA
authors.lastname: Beutler
authors.forename: Richard P
authors.initials: RP
authors.lastname: Johnson
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006873:Hydroquinones / Q000737:chemistry*; D008872:Microwaves; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D013816:Thermodynamics; D018808:Transcription Factor AP-1 / Q000037:antagonists & inhibitors* / Q000737:chemistry*
chemical_list: D006873:Hydroquinones; D018808:Transcription Factor AP-1