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

Hong, Hyo Jeong;Lee, Jae In

  • Received : 2014.08.06
  • Accepted : 2014.09.25
  • Published : 2014.12.20

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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