P-28 抗菌活性化合物botcinin類の不斉全合成研究(ポスター発表の部)
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概要
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Botcinins isolated from Botrytic cinerea, have growth inhibition activity against some plants. These compounds have peculiar structure including pyranopyranone ring and all of the carbon atoms except carbonyl carbon possess chiral center. Structures of botcinic acid and botcinin E^1 correspond to the re-assigned ones of botocinolide and 2-epibotcinolide. Recently, we have reported the enantioselective synthesis of the protected 2-epibotcinolide and we revealed that the presumed 9-membered lactone ring of botocinolide and 2-epibotcinolide are too unstable to be in nature. In this presentation, we will show the stereoselective synthetic studies of botcinins. A retro-synthetic route of botcinins is depicted in Scheme 1. The side-chain could be constructed by the aldol reaction of 2 with 3 followed by chain elongation. The pyranopyranone derivative 4 might be prepared from 5 using the aldol-type cyclization. Cyclic ether 5 could be constructed from 6 using the 6-endo ring closure accompanied with the acid catalyzed epoxide ring opening. Epoxy alcohol 6 might be formed by the Katsuki-Sharpless asymmetric epoxydation of allylic alcohol 7. Olefin 7 might be prepared from lactic acid derivative 9 by successive protocols such as aldol, Horner-Wadsworth-Emmons and other several reactions. We have synthesized the side-chain moiety and pyranopyranone derivative based on the above retro-synthetic route. Since the stereochemistry of the formed pyranopyranone derivative was determined to be unnatural configuration, we examine to adjust the structure by suitable epimerization.
- 天然有機化合物討論会の論文
- 2007-08-24
著者
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福井 博喜
東京理科大学理学部
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椎名 勇
東京理科大学理学部
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池田 達彦
東理大理
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鈴木 亮介
東理大理
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福井 博喜
東理大理
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梅崎 優真
東理大理
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辻 敬介
東理大理
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椎名 勇
東理大理
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椎名 勇
Department Of Applied Chemistry Faculty Of Science Tokyo University Of Science
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