Jaclyn Chau, Sanjia Xu, M. Ciufolini
Nov 11, 2013
Citations
0
Influential Citations
14
Citations
Journal
The Journal of organic chemistry
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.