Angiogenesis inhibitor epoxyquinol a: total synthesis and inhibition of transcription factor NF-kappaB.
[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.
Li
Chaomin
C
Department of Chemistry and Center for Streamlined Synthesis, Boston University, Massachusetts 02215, USA.
Bardhan
Sujata
S
Pace
Emily A
EA
Liang
Mei-Chih
MC
Gilmore
Thomas D
TD
Porco
John A
JA
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
D020533:Angiogenesis Inhibitors; D004852:Epoxy Compounds; D006873:Hydroquinones; D016328:NF-kappa B; C455959:epoxyquinol A