Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 20, Pages 10353-10358Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b01641
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Funding
- Natural Science Foundation of Jiangsu Province [BK2012676]
- Major Program of Natural Science Foundation [12KJA150005]
- PAPD of Jiangsu Higher Education Institutions
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An intramolecular [4 + 2] cycloaddition reaction of o-quinonemethides generated from salicylaldehydes and alpha-prenylated alcohols is described. In the presence of a catalytic amount of benzenesulfonic acid (BSA), the reaction proceeded smoothly in EtOH to afford furo[3,2-c]benzopyrans through a three-bond forming process in moderate to excellent yields with high diastereoselectivity. This reaction provides a simple and straightforward protocol to efficiently construct furo[3,2-c]benzopyran skeletons. A possible mechanism involving hemiacetal formation/hetero-Diels Alder reaction is proposed to rationalize the observed results.
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