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, Yusuf; BALAYDIN, Halis; Goksu, Süleyman; ŞAHİN, Ertan; MENZEK, Abdullah

doi:10.1002/hlca.200900300

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, cilt.93, sa.6, ss.1127-1135, 2010 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 93 Sayı: 6
Basım Tarihi: 2010
Doi Numarası: 10.1002/hlca.200900300
Dergi Adı: HELVETICA CHIMICA ACTA
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.1127-1135
Atatürk Üniversitesi Adresli: Evet

Özet

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.