title: Angiogenesis inhibitor epoxyquinol a: total synthesis and inhibition of transcription factor NF-kappaB.
abstract: [reaction: see text] The asymmetric synthesis of the natural product (+)-epoxyquinol A (1) and related epoxyquinoid dimers, employing a cascade oxidation/electrocyclization/Diels-Alder dimerization sequence, is reported. In addition, we show that 1 and related molecules inhibit activation of the transcription factor NF-kappaB.
authors.affiliation: Department of Chemistry and Center for Streamlined Synthesis, Boston University, Massachusetts 02215, USA.
authors.forename: Chaomin
authors.initials: C
authors.lastname: Li
authors.forename: Sujata
authors.initials: S
authors.lastname: Bardhan
authors.forename: Emily A
authors.initials: EA
authors.lastname: Pace
authors.forename: Mei-Chih
authors.initials: MC
authors.lastname: Liang
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Gilmore
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D020533:Angiogenesis Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D016328:NF-kappa B / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D020533:Angiogenesis Inhibitors; D004852:Epoxy Compounds; D006873:Hydroquinones; D016328:NF-kappa B; C455959:epoxyquinol A