4842-56-2Relevant articles and documents
A versatile synthesis of O-desmethylangolensin analogues from methoxy-substituted benzoic acids
Hong, Hyo Jeong,Lee, Jae In
, p. 569 - 574 (2015/02/05)
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.
Regioselectivity of methylation of O-demethylangolensin [1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one]. An expedient synthesis of angolensin
Waehaelae, Kristiina,Jokela, Tuija,Salakka, Auli,Kaltia, Seppo,Mesilaakso, Markku
, p. 642 - 644 (2007/10/03)
1-(2,4-Dihydroxyphenyl)-2-(4-hydroxyphenyl)propan-1-one (1), also known as 2',4',4''-trihydroxy-α-methyldeoxybenzoin or O-demethylangolensin (ODMA), is regioselectively 4-O-alkylated at ring B via the triphenolate anion by one equivalent of methyl iodide
A Facile Synthesis of α-Methyldesoxybenzoins Including Racemates of Natural Angolensin, 2-O-Methylangolensin and 4-O-Methylangolensin
Jain, A. C.,Paliwal, Poonam
, p. 985 - 988 (2007/10/02)
Methylation of four different 2-hydroxydesoxybenzoins ( 1a, 1c, 1d, 1f) separately with methyl iodide in the presence of dry potassium carbonate and acetone at 35-40 deg C affords both C-methyl-(2a, 2d) and O-methyl-(1b, 1e) derivatives.However, 1a provid