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

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 generali...

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Bibliographic Details
Published inOrganic letters Vol. 18; no. 14; pp. 3450 - 3453
Main Authors Mahajan, Pankaj S, Humne, Vivek T, Tanpure, Subhash D, Mhaske, Santosh B
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.07.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ROUTE
EPSILON-CAPROLACTAM
OXAZIRIDINES
MECHANISM
INDOLOQUINOLINONES
CYCLOHEXANONE OXIME
KETOXIMES
N BOND FORMATION
DERIVATIVES
AMIDES
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Summary: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.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.6b01634