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

被引：13

作者：

Asano, M ^{[1
]}

Nagasawa, C ^{[1
]}

Suzuki, M ^{[1
]}

Nishiyama, S ^{[1
]}

Sugai, T ^{[1
]}

机构：

[1] Keio Univ, Dept Chem, Yokohama, Kanagawa 2238522, Japan

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 2005年 / 69卷 / 01期

关键词：

cytoxazone; oxazolidinone; azidohydroxylation; nitrosation; deaminocyclization;

D O I：

10.1271/bbb.69.145

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页码：145 / 148

页数：4

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