title: Phenylboronic acid mediated triple condensation reactions of phloroglucinol and unsaturated carbonyl compounds.
abstract: [reaction: see text] A remarkable phenylboronic acid mediated triple condensation reaction of phloroglucinol (1,3,5-trihydroxybenzene) with a series of alpha,beta-unsaturated carbonyl compounds is reported. This experimentally simple reaction afforded novel C3-symmetric 2H-chromene derivatives. These derivatives represent structural analogues of the natural product xyloketal A, which has been reported to be a potent inhibitor of acetylcholine esterase.
authors.affiliation: Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia V5A 1S6, Canada.
authors.forename: Jeremy D
authors.initials: JD
authors.lastname: Pettigrew
authors.forename: Jay A
authors.initials: JA
authors.lastname: Cadieux
authors.forename: Simon S S
authors.initials: SS
authors.lastname: So
authors.forename: Peter D
authors.initials: PD
authors.lastname: Wilson
mesh_terms: D000110:Acetylcholinesterase / Q000378:metabolism; D001578:Benzopyrans / Q000737:chemistry; D001897:Boronic Acids / Q000737:chemistry*; D002384:Catalysis; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D010696:Phloroglucinol / Q000138:chemical synthesis* / Q000494:pharmacology; D011714:Pyrans / Q000737:chemistry
chemical_list: D001578:Benzopyrans; D001897:Boronic Acids; D002800:Cholinesterase Inhibitors; D011714:Pyrans; C438053:xyloketal A; D010696:Phloroglucinol; D000110:Acetylcholinesterase; C010686:benzeneboronic acid