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


Akbaba Y., Balaydin H. T. , Goksu S., ŞAHİN E., MENZEK A.

HELVETICA CHIMICA ACTA, vol.93, no.6, pp.1127-1135, 2010 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 93 Issue: 6
  • Publication Date: 2010
  • Doi Number: 10.1002/hlca.200900300
  • Title of Journal : HELVETICA CHIMICA ACTA
  • Page Numbers: pp.1127-1135

Abstract

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.