Phenylboronic acid mediated triple condensation reactions of phloroglucinol and unsaturated carbonyl compounds.
[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.
Pettigrew
Jeremy D
JD
Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia V5A 1S6, Canada.
Cadieux
Jay A
JA
So
Simon S S
SS
Wilson
Peter D
PD
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
D001578:Benzopyrans; D001897:Boronic Acids; D002800:Cholinesterase Inhibitors; D011714:Pyrans; C438053:xyloketal A; D010696:Phloroglucinol; D000110:Acetylcholinesterase; C010686:benzeneboronic acid