Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization.
J Org Chem
; 76(8): 2577-84, 2011 Apr 15.
Article
em En
| MEDLINE
| ID: mdl-21401026
ABSTRACT
Enantioselective syntheses of the azaphilone natural products (+)-sclerotiorin and (+)-8-O-methylsclerotiorinamine that possess the natural R-configuration at the quaternary center are reported. The syntheses were accomplished using copper-mediated asymmetric dearomatization employing bis-µ-oxo copper complexes prepared from readily available (+)-sparteine surrogates. Of note, site-selective O-methylation of a vinylogous pyridone was used to access the isoquinolin-6(7H)-one core of (+)-8-O-methylsclerotiorinamine.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Esparteína
/
Benzopiranos
/
Produtos Biológicos
/
Cobre
/
Isoquinolinas
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2011
Tipo de documento:
Article