title: Radical Beckmann Rearrangement and Its Application in the Formal Total Synthesis of Antimalarial Natural Product Isocryptolepine via C-H Activation.
abstract: 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 (18)O-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.
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune 411 008, India.
authors.forename: Pankaj S
authors.initials: PS
authors.lastname: Mahajan
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune 411 008, India.
authors.forename: Vivek T
authors.initials: VT
authors.lastname: Humne
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune 411 008, India.
authors.forename: Subhash D
authors.initials: SD
authors.lastname: Tanpure
authors.affiliation: Division of Organic Chemistry, CSIR-National Chemical Laboratory , Pune 411 008, India.
authors.forename: Santosh B
authors.initials: SB
authors.lastname: Mhaske
mesh_terms: D000645:Ammonium Sulfate / Q000737:chemistry; D000962:Antimalarials / Q000138:chemical synthesis*; D002384:Catalysis; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D016166:Free Radical Scavengers / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D011804:Quinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000962:Antimalarials; D016166:Free Radical Scavengers; D005609:Free Radicals; D026121:Indole Alkaloids; D011804:Quinolines; C577868:isocryptolepine; C031276:ammonium peroxydisulfate; D000645:Ammonium Sulfate; D004121:Dimethyl Sulfoxide