Assembly of a key dienic intermediate for tetrodotoxin via a Machetti-DeSarlo reaction.
J Org Chem
; 78(23): 11901-10, 2013 Dec 06.
Article
em En
| MEDLINE
| ID: mdl-24161206
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.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Tetrodotoxina
/
Derivados de Benzeno
Idioma:
En
Ano de publicação:
2013
Tipo de documento:
Article