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Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C–H Activation

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journal contribution
posted on 01.07.2016, 22:29 by Pankaj S. Mahajan, Vivek T. Humne, Subhash D. Tanpure, Santosh B. Mhaske
The Beckmann rearrangement of ketoximes, mediated by ammonium persulfate-dimethyl sulfoxide as a reagent, has been achieved under neutral conditions. Based on the radical trapping and 18O-labeling experiments, the transformation follows a mechanism involving a radical pathway. The scope and generality of the developed protocol has been demonstrated by 19 examples. The developed protocol and Pd-catalyzed intramolecular double C–H activation were used as key steps in the formal total synthesis of antimalarial natural product isocryptolepine.