A novel approach to cis-jasmone and dihydrojasmone from 2-(2-benzothiazolythio)-2-(3-oxobutyl)oct-5-en(or -an)oic acid by electrolytic procedure.
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概要
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<I>cis</I>-Jasmone (<B>7a</B>) and dihydrojasmone (<B>7b</B>) have been synthesized by facile five-step processes starting from methyl acetoacetate involving electrolysis procedure. Methyl 2-(2-benzothiazolylthio)oct-5-en(or -an)oate, prepared from methyl 2-acetyloct-5-en(or -an)oate (<B>1</B>) by the reaction with the <I>N</I>-(2-benzothiazolylthio)morpholine, were allowed to react with methyl vinyl ketone, leading to the Michael adducts <B>4</B>. After hydrolysis of <B>4</B>, the corresponding acids <B>5</B> were electrolyzed to afford the desired 1,4-diketone <B>6</B> in 45–48% overall yields (based on <B>1</B>), whose base-catalyzed cyclization gave <B>7</B> smoothly.
- 公益社団法人 日本化学会の論文
著者
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NOKAMI Junzo
Okayama University of Science
-
Torii Sigeru
Department Of Applied Chemistry Faculty Of Engineering Okayama University
-
Tanaka Hideo
Department Of Applied Chemistry Faculty Of Engineering Okayama University
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Kobayasi Yuichi
Department of Industrial Chemistry, School of Engineering, Okayama University
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Kawata Mikio
Okayama University of Science
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