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http://dx.doi.org/10.5012/jkcs.2014.58.6.569

A Versatile Synthesis of O-Desmethylangolensin Analogues from Methoxy-Substituted Benzoic Acids  

Hong, Hyo Jeong (Department of Chemistry, Duksung Women's University)
Lee, Jae In (Department of Chemistry, Duksung Women's University)
Publication Information
Journal of the Korean Chemical Society / v.58, no.6, 2014 , pp. 569-574 More about this Journal
Abstract
The synthesis of O-desmethylangolensin (O-DMA) analogues from methoxy-substituted benzoic acids was described. Treatment of methoxy-substituted benzoic acids with 2 equiv of ethyllithium afforded methoxypropiophenones, which were subsequently transformed to ethyl 2-(methoxyphenyl)propionates via 1,2-rearrangement of the methoxyphenyl group using $Pb(OAc)_4/HClO_4$ in triethyl orthoformate. After hydrolysis with KOH, the 2-(methoxyphenyl)propionic acids were reacted with di-2-pyridyl carbonate to afford 2-pyridyl 2-(methoxyphenyl)propionates, which were acylated with methoxy-substituted phenylmagnesium bromides to give methoxy-${\alpha}$-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.
Keywords
O-Desmethylangolensin; Condensation; Substitution; Rearrangement; Demethylation;
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