A new synthesis of pyrocin and related compounds.

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概要

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• A new synthesis of pyrocin (<B>1</B>) and related compounds is described. The reaction of 2-benzoyl-4,4-dimethyl-2-buten-4-olide (<B>5b</B>) with 2-methyl-1-propenylmagnesium bromide (<B>6</B>) in the presence of CuCl gave α-benzoylpyrocin (<B>7b</B>) in 90% yield. The product of <B>7b</B> with a specific rotation of +2.43° was obtained when the reaction was carried out in the presence of (−)-sparteine. α-Acetylpyrocin (<B>7a</B>) was prepared in the similar manner in 63% yield. The treatment of <B>7a</B> and that of <B>7b</B> with ethanolic sodium ethoxide gave <B>1</B> in 65% and 81% yields, respectively. The reaction of <B>1</B> with large excess of SOCl<SUB>2</SUB> in absolute ethanol gave ethyl 3-(1-chloro-1-methylethyl)-5-methyl-4-hexenoate (<B>8</B>) in 82% yield. Similar treatment of <B>7</B> with SOCl<SUB>2</SUB> gave ethyl 2-substituted-4-(2-methyl-1-propenyl)-5,5-dimethyl-4,5-dihydrofuran-3-carboxylate (<B>12</B>). Compound <B>8</B> was transformed to ethyl <I>trans</I>-(±)-chrysanthemate (<B>2</B>) in 75% yield.

• 公益社団法人 日本化学会の論文

著者

• Tsuboi Sadao

  Department Of Applied Chemistry Faculty Of Engineering Okayama University

• Sakai Takashi

  Department Of Applied Chemistry Faculty Of Engineering Okayama University

• Takeda Akira

  Department Of Gastroenterology Osaka General Medical Center

• Shinohara Shohei

  Department of Synthetics Chemistry, School of Engineering, Okayama University

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