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
