Radical beckmann rearrangement and its application in the formal total synthesis of antimalarial natural product isocryptolepine via C-H activation

TitleRadical beckmann rearrangement and its application in the formal total synthesis of antimalarial natural product isocryptolepine via C-H activation
Publication TypeJournal Article
Year of Publication2016
AuthorsMahajan, PS, Humne, VT, Tanpure, SD, Mhaske, SB
JournalOrganic Letters
Volume18
Issue14
Pagination3450-3453
Date PublishedJUL
ISSN1523-7060
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 O-18-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.

DOI10.1021/acs.orglett.6b01634
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)6.732
Divison category: 
Organic Chemistry