4.3 Article

Total Synthesis of the Biologically Active, Naturally Occurring 3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol and Regioselective O-Demethylation of Aryl Methyl Ethers

Journal

HELVETICA CHIMICA ACTA
Volume 93, Issue 6, Pages 1127-1135

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/hlca.200900300

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Funding

  1. Scientific and Technological Research Council of Turkey (TUBITAK) [TBAG-107T/348]
  2. Ataturk University

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3,4-Dibromo-5-[2-bromo-3,4-dihydroxy-6-(methoxymethyl)benzyl]benzene-1,2-diol (2), a natural product, has been synthesized for the first time starting from (3-bromo-4,5-dimethoxyphenyl)methanol (5) in five steps and with an overall yield of 34%. The reaction of some methoxymethyl-substituted aryl methyl ethers with BBr3, followed by the addition of MeOH, afforded the corresponding methoxymethyl-substituted arylphenols in high yields.

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