| Title | Assembly of a Key Dienic Intermediate for Tetrodotoxin via a Machetti-DeSarlo Reaction |
| Publication Type | Journal Article |
| Year of Publication | 2013 |
| Authors | Chau, J, Xu, S, Ciufolini, MA |
| Journal | JOURNAL OF ORGANIC CHEMISTRY |
| Volume | 78 |
| Pagination | 11901-11910 |
| Date Published | DEC 6 |
| ISSN | 0022-3263 |
| Abstract | A route to a racemic diene intermediate for the synthesis of tetrodotoxin is described. Key steps of the sequence leading to such a compound include the oxidative amidation of a phenol, a Cu(II)-catalyzed cyclocondensation of a nitroketone with an olefin (Machetti-DeSarlo reaction), and a nucleophilic fragmentation of the resulting isoxazoline. Several unusual reactions encountered in the course of this study are thoroughly discussed. |
| DOI | 10.1021/jo401960p |
