Sequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo[b,d]pyran-6-ones related to ellagic acid

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dc.contributor.authorAlo, B.I.
dc.contributor.authorKandil, A.
dc.contributor.authorPatil, P.A.
dc.contributor.authorSharp, M.J.
dc.contributor.authorSiddiqui, M.A.
dc.contributor.authorSnieckus, V.
dc.contributor.authorJosephy, P.D.
dc.date.accessioned2019-08-30T08:21:38Z
dc.date.available2019-08-30T08:21:38Z
dc.date.issued1990-08
dc.description.abstractA general regiospecific synthesis of dibenzo[ b,d]pyran-6-one derivatives la,c and 8a-i related to ellagic acid is described (Scheme I, Table I). The sequence involves directed ortho metalation-boronation of benzamides 4 to give the arylboronic acids 5, which, upon palladium-catalyzed cross-coupling with alkoxybromobenzenes 6 leads to the biphenylamides 7. BBr3 demethylation followed by acid-catalyzed cyclization affords pyranone 8. In this manner, the naturally occurring dibenzopyranones la, autumnariol (IC), and the heterocyclic analogue 13 (Scheme 111) were efficiently prepared.en_US
dc.identifier.citationAlo, B. I., Kandil, A., Patil, P. A., Sharp, M. J., Siddiqui, M. A., Snieckus, V., & Josephy, P. D. (1991). Sequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo [b, d] pyran-6-ones related to ellagic acid. The Journal of Organic Chemistry, 56(12), 3763-3768.en_US
dc.identifier.urihttps://ir.unilag.edu.ng/handle/123456789/4888
dc.language.isoenen_US
dc.subjectResearch Subject Categories::NATURAL SCIENCES::Chemistry::Organic chemistryen_US
dc.subjectcross-coupling reactionsen_US
dc.subjectdibenzo[b,d]pyran-6-onesen_US
dc.subjectellagic aciden_US
dc.titleSequential directed ortho metalation-boronic acid cross-coupling reactions. A general regiospecific route to oxygenated dibenzo[b,d]pyran-6-ones related to ellagic aciden_US
dc.typeArticleen_US
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