Catalytic asymmetric total syntheses of quinine and quinidine.
J Am Chem Soc
; 126(3): 706-7, 2004 Jan 28.
Article
em En
| MEDLINE
| ID: mdl-14733531
ABSTRACT
The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high selectivity.
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Base de dados:
MEDLINE
Assunto principal:
Quinidina
/
Quinina
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2004
Tipo de documento:
Article
País de afiliação:
Estados Unidos