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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
Author(s) -
Akbaba Yusuf,
Türker Balaydın Halis,
Göksu Süleyman,
Şahin Ertan,
Menzek Abdullah
Publication year - 2010
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900300
Subject(s) - chemistry , yield (engineering) , demethylation , regioselectivity , aryl , benzene , diol , methanol , medicinal chemistry , natural product , organic chemistry , stereochemistry , catalysis , biochemistry , gene expression , materials science , dna methylation , alkyl , metallurgy , gene
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 BBr 3 , followed by the addition of MeOH, afforded the corresponding methoxymethyl‐substituted arylphenols in high yields.