Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. In an article, author is Padwa, A, once mentioned the application of 2210-74-4, Name is 1-(2-Methoxyphenoxy)-2,3-epoxypropane, molecular formula is C10H12O3, molecular weight is 180.2005, MDL number is MFCD00190158, category is dioxole. Now introduce a scientific discovery about this category, Quality Control of 1-(2-Methoxyphenoxy)-2,3-epoxypropane.
Tandem Pummerer-Diels-Alder reaction sequence. A novel cascade process for the preparation of 1-arylnaphthalene lignans
The alpha-thiocarbocation generated from the Pummerer reaction of an o-benzoyl-substituted sulfoxide is intercepted by the adjacent keto group to produce an alpha-thio isobenzofuran as a transient intermediate which undergoes a subsequent Diels-Alder cycloaddition with added dienophiles. Acid-catalyzed ring-opening of the cycloadduct followed by aromatization gave an arylnaphthalene derivative. With acetylenic dienophiles, the tandem cyclization-cycloaddition sequence provided tetralones which result from a pinacol-type rearrangement of the primary cycloadducts. The versatility of the approach is highlighted through the synthesis of taiwanin C and E and justicidin E. The alpha-thiocarbocation generated from the Pummerer reaction of benzo[1,3]dioxol-5-yl-[6-(ethylsulfinyl)methyl]benzo[1,3]dioxol-5-yl) is intercepted by the adjacent keto group to produce an alpha-thioisobenzofuran as a transient intermediate which undergoes a subsequent Diels-Alder cycloaddition with dimethyl maleate. The initially formed Diels-Alder cycloadduct was readily converted to 5-benzo[1,3]dioxol-5-yl-8-(ethylthio)naphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid dimethyl ester by lass of water on treatment with p-toluenesulfonic acid. Desulfurization of the thionaphthalene with Ra/Ni followed by hydrolysis of the less hindered methyl ester afforded 5-benzo[1,3]dioxol-5-ylnaphtho[2,3-d][1,3]dioxole-6,7-dicarboxylic acid 6-methyl ester which was further transformed into taiwanin C and justicidin E in good yield, Oxidation of the initial Diels-Alder cycloadduct with NaIO4 in the presence of RuCl3 followed by extrusion of ethyl sulfinate gave a naphthol derivative which can be converted into taiwanin E.
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Reference:
1,3-Benzodioxole – Wikipedia,
,Dioxole | C3H4O2 – PubChem