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 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 93 Issue: 6
  • Publication Date: 2010
  • Doi Number: 10.1002/hlca.200900300
  • Journal Name: HELVETICA CHIMICA ACTA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1127-1135
  • Recep Tayyip Erdoğan University Affiliated: No

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.