A highly stereoselective synthesis of (E)-enol lactones by the Wittig reaction of cyclic anhydrides with (.ALPHA.-alkoxycarbonyl-ethylidene)triphenylphosphorane.

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概要

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• Reactions of glutaric anhydride and methyl- or phenyl-substituted ones with (α-alkoxycarbonylethylidene)triphenylphosphorane (<B>2a</B>, ethoxy; <B>2b</B>, <I>t</I>-butoxy) gave the corresponding 6-alkoxycarbonyl-5-hepten-5-olides (<B>3</B>) and 6-alkoxycarbonyl-4-hepten-5-olides in good yields. The reaction proceeded highly stereoselectively to give (<I>E</I>)-<B>3</B>. The stereochemistry of <B>3</B> was determined by an X-ray crystallographic analysis. The reaction of adipic anhydride with <B>2a</B> afforded 7-ethoxycarbonyl-5-octen-6-olide, 7-ethoxycarbonyl-5,6-octadienoic acid, and (4<I>E</I>, 6<I>E</I>)-7-ethoxycarbonyl-4,6-octadienoic acid. A treatment of nonanedioic anhydride with <B>2a</B> gave 10-ethoxycarbonyl-8,9-undecadienoic acid, (7<I>E</I>,9<I>E</I>)-10-ethoxycarbonyl-7,9-undecadienoic acid, and diethyl 2-methyl-2,4-undecadienedioate in low yields.

• 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

• Fukuyama Keiichi

  Department Of Biological Sciences Graduate School Of Science Osaka University

• Takeda Akira

  Department Of Gastroenterology Osaka General Medical Center

• Wada Hiroshi

  Department Of Bioengineering And Robotics Tohoku University

• Wada Hiroshi

  Department of Synthetic Chemistry, School of Engineering, Okayama University

• Fukumoto Hirohumi

  Department of Synthetic Chemistry, School of Engineering, Okayama University

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