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From Roquefortine C to Roquefortine L: Formation of a Complex Nitrone with Simple Oxidizing Agents

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The oxidation of roquefortine C to the nitrone roquefortine L was investigated using a number of different electrophilic oxidizing reagents. mCPBA and Oxone were shown to be the most effective… Click to show full abstract

The oxidation of roquefortine C to the nitrone roquefortine L was investigated using a number of different electrophilic oxidizing reagents. mCPBA and Oxone were shown to be the most effective in achieving this transformation, while unfavorable steric interactions precluded oxidation by bulky reagents such as Davis oxaziridine. Finally, each of the oxidants was shown to promote aromatic hydroxylation following the synthesis of the nitrone functionality.

Keywords: roquefortine roquefortine; complex nitrone; formation complex; nitrone simple; roquefortine; roquefortine formation

Journal Title: Israel Journal of Chemistry
Year Published: 2017

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