Phosphate tether-mediated approach to the formal total synthesis of (-)-salicylihalamides A and B.
J Org Chem
; 76(10): 3909-16, 2011 May 20.
Article
em En
| MEDLINE
| ID: mdl-21504150
ABSTRACT
A concise formal synthesis of the cytotoxic macrolides (-)-salicylihalamides A and B is reported. Key features of the synthetic strategy include a chemoselective hydroboration, highly regio- and diastereoselective methyl cuprate addition, Pd-catalyzed formate reduction, and an E-selective ring-closing metathesis to construct the 12-membered macrocycle subunit. Overall, two routes have been developed from a readily prepared bicyclic phosphate (4 steps), a 13-step route and a more efficient 9-step sequence relying on regioselective esterification of a key diol.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Fosfatos
/
Compostos Bicíclicos Heterocíclicos com Pontes
Idioma:
En
Ano de publicação:
2011
Tipo de documento:
Article