Radical beckmann rearrangement and its application in the formal total synthesis of antimalarial natural product isocryptolepine via C-H activation
Title | Radical beckmann rearrangement and its application in the formal total synthesis of antimalarial natural product isocryptolepine via C-H activation |
Publication Type | Journal Article |
Year of Publication | 2016 |
Authors | Mahajan, PS, Humne, VT, Tanpure, SD, Mhaske, SB |
Journal | Organic Letters |
Volume | 18 |
Issue | 14 |
Pagination | 3450-3453 |
Date Published | JUL |
ISSN | 1523-7060 |
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. |
DOI | 10.1021/acs.orglett.6b01634 |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 6.732 |
Divison category:
Organic Chemistry