著者

的場 勝英 利根 斉 新浜 光一 後藤 文孝 坂 雅之 南川 純一

出版者

The Society of Synthetic Organic Chemistry, Japan

雑誌

有機合成化学協会誌 (ISSN:00379980)

巻号頁・発行日

vol.57, no.5, pp.407-414, 1999-05-01 (Released:2009-11-16)

参考文献数

3

被引用文献数

1 6

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An efficient and practical synthetic route to OPC-15161 (1), a novel inhibitor of superoxide anion generation, is described. Intensive survey on pyrazine ring manipulation has led to the development of multi-kilo synthetic pathway, in which beneficial use of a nitrogen protecting group is the key to the problematic cyclization and O-methylation process, both being carried out in one-pot operation. Thus, the synthesis proceeds in 40% overall yield in four steps from tryptophan methyl ester with simple operation and without chromatographic purification, which also opens a general route for the preparation of related 5-alkoxypyrazin-2 (1H) -one 4-oxide such as emeheterone.

著者

的場 勝英 浜島 健二 山崎 高応

出版者

公益社団法人日本薬学会

雑誌

藥學雜誌 (ISSN:00316903)

巻号頁・発行日

vol.94, no.11, pp.1459-1467, 1974-11-25

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2-Ethoxy-3-methoxy-2-cyclohexenone (II) and 2,3,5-trimethoxy-2-cyclohexenone (III) were prepared from pyrogallol in a satisfactory yield. II was reduced with lithium aluminium hydride to 2-ethoxy-3-methoxy-2-cyclohexenol (XXV), which was not so stable. III was reduced under the same condition to 2,5-dimethoxy-2-cyclohexenol (XXIX) and 2,3,5-trimethoxy-2-cyclohexenol (XXX). XXX was relatively stable but was not so stable as the reduced product of acutumine (I).