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Journal of the Korean Chemical Society (JKCS)

ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 58, Number 6
JKCSEZ 58(6)
December 20, 2014

Title	A Versatile Synthesis of O-Desmethylangolensin Analogues from Methoxy-Substituted Benzoic Acids
Author	Hyo Jeong Hong, Jae In Lee*
Keywords	O-Desmethylangolensin, Condensation, Substitution, Rearrangement, Demethylation
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/HClO4 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-α-methyldesoxybenzoins. The methoxy groups of these compounds were selectively or fully demethylated using boron tribromide to give diverse O-DMA analogues in high yields.
Page	569 - 574
Full Text	PDF

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