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

Autor: Subhash D. Tanpure, Vivek T. Humne, Pankaj S. Mahajan, Santosh B. Mhaske
Rok vydání: 2016
Předmět:
Zdroj: ChemInform. 47
ISSN: 0931-7597
DOI: 10.1002/chin.201648028
Popis: 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.
Databáze: OpenAIRE