Synthetic studies on quinoxaline antibiotics. Synthesis of quinoxaline-2-carbonyl tetradepsipeptide derivatives related to triostin A.
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概要
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The synthesis is described of four quinoxaline-2-carbonyl (Qxc) tetradepsipeptide derivatives, Qxc–D-Ser[Z–MeCys(Bzl)–MeVal]–Ala–OH, Qxc–D-Ser[Bpoc–MeCys(Bzl)–MeVal]–Ala–OBu<I><SUP>t</SUP></I> (<B>2</B>), Qxc-D-Ser(Z–MeVal)–Ala–MeCys(Bzl)–OH, and Qxc–D-Ser(Bpoc–MeVal)–Ala–MeCys(Bzl)–OBu<I><SUP>t</SUP></I>, corresponding to the partial structure of a quinoxaline antibiotic, triostiin A. The Qxc group was introduced at the dipeptide or tripeptide stage with Qxc–ONp as acylating agent. Qxc–D-Ser–Ala–OBu<I><SUP>t</SUP></I> and Qxc–D-Ser–Ala–MeCys(Bzl)–OBu<I><SUP>t</SUP></I> were acylated with Z–MeVal–OH by using <I>p</I>-toluenesulfonyl chloride as activating agent to give the desired depsipeptides in excellent yields, whereas the acylation with Bpoc–MeVal–OH by the same procedure was unsuccessful. The latter could be achieved by the <I>N</I>,<I>N</I>′-carbonyldiimidazole method, though the yields were relatively low. The treatment of compound <B>2</B> with an aqueous acetic acid–formic acid mixture for removal of the Bpoc group brought about concomitant formation of <I>cyclo</I>[–MeCys(Bzl)–MeVal–].
- 公益社団法人 日本化学会の論文
著者
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Inouye Ken
Shionogi Research Laboratories, Shionogi & Co., Ltd.
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Otsuka Hideo
Shionogi Research Laboratories, Shionogi & Co., Ltd.
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Shin Masaru
Shionogi Research Laboratory, Shionogi & Co., Ltd.
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SHIN Masaru
Shionogi Laboratories, Shionogi and Co., Ltd.
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