Stereoselective Synthesis of a Promising Flower-Inducing KODA Analog, (9R,12S,13R,15Z)-9-Hydroxy-12,13-methylene-10-oxooctadec-15-enoic Acid
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- SHIMOMURA Shin
- Department of Bioresource Science, College of Agriculture, Ibaraki University
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- OYAMA Shuho
- Department of Bioresource Science, College of Agriculture, Ibaraki University
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- NAKANO Kyohei
- Department of Bioresource Science, College of Agriculture, Ibaraki University
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- HASEGAWA Morifumi
- Department of Bioresource Science, College of Agriculture, Ibaraki University
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- TOSHIMA Hiroaki
- Department of Bioresource Science, College of Agriculture, Ibaraki University
書誌事項
- タイトル別名
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- Stereoselective Synthesis of a Promising Flower-Inducing KODA Analog, (9<i>R</i>,12<i>S</i>,13<i>R</i>,15<i>Z</i>)-9-Hydroxy-12,13-methylene-10-oxooctadec-15-enoic Acid
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抄録
Stereoselective synthesis of a promising flower-inducing 9,10-ketol octadecadienoic acid (KODA) analog, (9R,12S,13R,15Z)-9-hydroxy-12,13-methylene-10-oxooctadec-15-enoic acid, was designed to obtain the desired stereoisomer via coupling between chiral sulfone and aldehyde segments. A known chiral cyclopropane derivative was converted to the sulfone segment via carbon-chain elongation and sulfonylation. Dec-9-en-1-ol was converted to the aldehyde segment, whose C-9 configuration was introduced by Sharpless asymmetric dihydroxylation. Coupling of the both segments and subsequent assembly gave the desired (9R,12S,13R,15Z)-analog. The (9S,12S,13R,15Z)-analog was also synthesized by using the enatiomeric aldehyde segment. This strategy made it possible to synthesize the remaining stereoisomeric analogs.
収録刊行物
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- Bioscience, Biotechnology, and Biochemistry
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Bioscience, Biotechnology, and Biochemistry 77 (6), 1354-1357, 2013
公益社団法人 日本農芸化学会
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詳細情報 詳細情報について
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- CRID
- 1390001206479783680
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- NII論文ID
- 10031184713
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- NII書誌ID
- AA10824164
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- COI
- 1:STN:280:DC%2BC3sjhtFWntQ%3D%3D
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- ISSN
- 13476947
- 09168451
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- NDL書誌ID
- 024647363
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- PubMed
- 23748793
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
- PubMed
- CiNii Articles
- KAKEN
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- 抄録ライセンスフラグ
- 使用不可