1486512-72-4Relevant academic research and scientific papers
Assembly of a key dienic intermediate for tetrodotoxin via a Machetti-DeSarlo reaction
Chau, Jaclyn,Xu, Sanjia,Ciufolini, Marco A.
, p. 11901 - 11910 (2014/01/06)
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.
