Oxidation of d-Limonene with Selenium Dioxide-hydrogen Peroxide |
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Authors: | Masashi Sumimoto Toshio Suzuki Tainio Kondo |
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Institution: | Faculty of Agriculture, Kyushu University, Fukuoka |
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Abstract: | Oxidation of d-Iimonene with selenium dioxide-hydrogen peroxide affords (+)-l-hydroxyneodihydrocarveol as the major product formed via cis- and trans-limonene epoxide. Hydrolysis of the former epoxide is much faster than that of the latter, which can therefore be obtained in almost quantitative yield on acid hydrolysis of a mixture of cis- and trans-limonene epoxide (1:1) under mild condition.Minor significance of oxygenation in an allylic position to a trisubstituted double bond and the difference of accessibility of an allylic position to di- and trisubstituted double bond toward the oxidant were also observed. |
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Keywords: | Aspergillus fumigatus fumitremorgin secondary metabolite biosynthesis O-methyltransferase |
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