Total synthesis of 3,3′,4-tri- O-methylellagic acid from gallic acid

Total synthesis of 3,3′,4-tri- O-methylellagic acid has been described from commercially available gallic acid. Construction of the crucial unsymmetric Ar–Ar bond has been carried out in various methods such as Heck coupling, Heck coupling followed by oxidation or anionic Fries rearrangement, Suzuki...

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Bibliographic Details
Published inTetrahedron Vol. 63; no. 42; pp. 10454 - 10465
Main Authors Alam, Ashraful, Tsuboi, Sadao
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.10.2007
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
DIRECTED BIARYL SYNTHESIS
METALATION
CHIRAL NATURAL-PRODUCTS
COUPLING REACTION
CATALYZED CYCLIZATION
ARYL
INHIBITORS
ELLAGIC ACID
DERIVATIVES
ELLAGITANNIN
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Summary:Total synthesis of 3,3′,4-tri- O-methylellagic acid has been described from commercially available gallic acid. Construction of the crucial unsymmetric Ar–Ar bond has been carried out in various methods such as Heck coupling, Heck coupling followed by oxidation or anionic Fries rearrangement, Suzuki cross-coupling, etc., but all the attempts were unsuccessful. Then, finally it has been achieved by intramolecular Ullmann coupling reaction. Total synthesis of 3,3,′4-tri- O-methylellagic acid has been achieved from gallic acid. Construction of crucial unsymmetric Ar–Ar bond was tried in various ways such as Ullmann cross-coupling, Suzuki cross-coupling, intramolecular Heck coupling, etc. But all the attempts were unsuccessful and finally it has been achieved by the intramolecular Ullmann coupling. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2007.07.103