Progress in the Synthesis of OPC-15161: Easy Access to Dioxygenated Pyrazine N-Oxide Structure

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• 作者：Hitoshi Tone ; Katsuhide Matoba ; Fumitaka Goto ; Yasuhiro Torisawa ; Takao Nishi ; and Jun-ichi Minamikawa
• 刊名：Organic Process Research & Development
• 出版年：2000
• 出版时间：September 2000
• 年：2000
• 卷：4
• 期：5
• 页码：312 - 317
• 全文大小：257K
• 年卷期：v.4,no.5(September 2000)
• ISSN：1520-586X

文摘

An improved synthetic route to OPC-15161 (1), a novel inhibitorof superoxide anion generation, is described. Choice of theprotecting group is the key to the second-generation synthesis.Usefulness of the 2-cyanoethyl (CE)-protecting group in ourprocess research is emphasized in comparison with that of otherprotecting groups. This process can be carried out in four stepswith 40% overall yield from tryptophan methyl ester, whichalso opens a general route for the preparation of the related5-alkoxypyrazin-2(1H)-one 4-oxides.