Short-step and scalable synthesis of (+/-)-cytoxazone.
Biosci Biotechnol Biochem
; 69(1): 145-8, 2005 Jan.
Article
en En
| MEDLINE
| ID: mdl-15665479
ABSTRACT
A five-step and scalable synthesis of racemic cytoxazone, a novel cytokine modulator, was accomplished in a total yield of 51% from p-methoxycinnamyl alcohol without any protective groups. The keystep was the new one-pot azidohydroxylation procedure by the combined use of NaN3-H2O2-CH3CN. The epoxidation of an olefin by means of an in situ-formed iminohydroperoxide worked well, accompanied by the concomitant regioselective ring opening reaction of the resulting highly reactive epoxide with an azide ion.
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Base de datos:
MEDLINE
Asunto principal:
Oxazoles
Idioma:
En
Revista:
Biosci Biotechnol Biochem
Asunto de la revista:
BIOQUIMICA
/
BIOTECNOLOGIA
Año:
2005
Tipo del documento:
Article
País de afiliación:
Japón