Acid-Catalyzed Rearrangement of Aryl-Substituted Homobenzoquinone Epoxides

The BF3-catalyzed reactions of diphenyl-substituted and endo-monophenyl-substituted homobenzoquinone epoxides proceeded through a regioselective oxirane ring opening followed by participation of a π-aryl transannular cyclization to give the tricyclic diketo alcohols. The conformationally semirigid e...

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Published inOrganic letters Vol. 9; no. 17; pp. 3421 - 3424
Main Authors Asahara, H, Kubo, E, Togaya, K, Koizumi, T, Mochizuki, E, Oshima, T
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 16.08.2007
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
EPOXIDATION
RING-OPENING REACTIONS
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Summary:The BF3-catalyzed reactions of diphenyl-substituted and endo-monophenyl-substituted homobenzoquinone epoxides proceeded through a regioselective oxirane ring opening followed by participation of a π-aryl transannular cyclization to give the tricyclic diketo alcohols. The conformationally semirigid ethano-bridged diphenyl-substituted homologues also provided similar diketo alcohols and the subsequent ring-expanded cycloheptenedione (via a subsequent 1,2-acyl migration associated with cyclopropane ring opening), depending on the methyl-substitution pattern of the quinone frame. However, the exo-monophenyl-substituted and the rigid biphenyl-2,2‘-diyl-substituted homobenzoquinone epoxides essentially remained unchanged.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol7014576