Phenylboronic acid mediated triple condensation reactions of phloroglucinol and unsaturated carbonyl compounds.

Org Lett

Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia V5A 1S6, Canada.

Published: February 2005

[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.

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http://dx.doi.org/10.1021/ol047578oDOI Listing

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