|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|
|Date Published||DEC 6|
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.