A practical synthesis of 5-lipoxygenase inhibitor MK-0633.
J Org Chem
; 75(12): 4154-60, 2010 Jun 18.
Article
em En
| MEDLINE
| ID: mdl-20486715
ABSTRACT
Practical, chromatography-free syntheses of 5-lipoxygenase inhibitor MK-0633 p-toluenesulfonate (1) are described. The first route used an asymmetric zincate addition to ethyl 2,2,2-trifluoropyruvate followed by 1,3,4-oxadiazole formation and reductive amination as key steps. An improved second route features an inexpensive diastereomeric salt resolution of vinyl hydroxy-acid 22 followed by a robust end-game featuring a through-process hydrazide acylation/1,3,4-oxadiazole ring closure/salt formation sequence to afford MK-0633 p-toluenesulfonate (1).
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Oxidiazóis
/
Benzenossulfonatos
/
Benzopiranos
/
Inibidores de Lipoxigenase
Idioma:
En
Ano de publicação:
2010
Tipo de documento:
Article