ol6b01634_si_001.pdf (2.18 MB)
Download file

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

Download (2.18 MB)
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.

History