The reaction of epoxyisophorone with ethyl acetoacetate under basic conditions

Treatment of epoxyisophorone ( 1) with ethyl acetoacetate under basic conditions resulted in the stereoselective formation of dihydroxybenzofuran 2 in moderate yield. This result is in contradiction to previous work where similar conditions were reported to afford a bicyclo [4.3.0]nonadienone via a...

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Bibliographic Details
Published in:Tetrahedron 2010-10, Vol.66 (40), p.8018-8020
Main Authors: Snowden, Roger L., Linder, Simon, Fuchs, Nicolas, Bernardinelli, Gérald
Format: Article
Language:English
Subjects:
Acetoacetate
Benzofuran
Chemistry
Epoxyisophorone
Exact sciences and technology
Furannulation
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:Treatment of epoxyisophorone ( 1) with ethyl acetoacetate under basic conditions resulted in the stereoselective formation of dihydroxybenzofuran 2 in moderate yield. This result is in contradiction to previous work where similar conditions were reported to afford a bicyclo [4.3.0]nonadienone via a putative Robinson annulation reaction. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.08.007