Short-step and scalable synthesis of (+-)-cytoxazone

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 epoxid...

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Veröffentlicht in:	Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2005-01, Vol.69 (1), p.145-148
Hauptverfasser:	Asano, M. (Keio Univ., Yokohama (Japan). Faculty of Science and Technology), Nagasawa, C, Suzuki, M, Nishiyama, S, Sugai, T
Format:	Artikel
Sprache:	eng
Schlagworte:	AZIDES azidohydroxylation Biological and medical sciences CHEMICAL SYNTHESIS CYTOKINES cytoxazone deaminocyclization Fundamental and applied biological sciences. Psychology Molecular Structure nitrosation Oxazoles - chemical synthesis oxazolidinone Stereoisomerism
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Beschreibung
Zusammenfassung:	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.
ISSN:	0916-8451 1347-6947
DOI:	10.1271/bbb.69.145