Synthesis of Chiral 3'-Hydroxy-γ-ionylideneacetic Acids (Organic Chemistry)
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概要
- 論文の詳細を見る
Four isomers of chiral 3'-hydroxy-γ-ionylideneacetic acid (3'-hydroxy-γ-acid), acidic metabolites of Cercospora cruenta, were synthesized from (+)-(S)-3-hydroxy-2, 2-dimethyl-1-cyclohexa-none as the chiral starting material. A [2.3]-sigmatropic rearrangement of (+)-(S)-3,3-dimethyl-4-tetrahydropyranyloxy-1-cyclohexenemethanol, which was followed by two steps of the Wittig reaction, gave (+)-(1'S,3'S)-(2E,4E)- and (+)-(1'S,3'S)-(2Z,4E)-3'-hydroxy-γ-acids. Oxidation and subsequent reduction of (+)-(1'S,3'S)-(2E,4E)-3'-hydroxy-γ-acid menthyl ester gave (-)-(1'S,3'R)-(2E,4E)- ester, which was isomerized to (-)-(1'S,3'R)-(2Z,4E)-ester by ultra violet irradiation.
- 社団法人日本農芸化学会の論文
- 1988-09-23
著者
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YAMAMOTO Hiroshi
Department of Macromolecular Science, Graduate School of Science, Osaka University
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YAMASHITA Kyohei
Department of Agricultural Chemistry, Faculty of Agriculture, Tohoku University
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Yamamoto H
Department Of Applied Biology Faculty Of Textile Science And Technology Shinshu University
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ORITANI Takayuki
Department of Applied Biological Chemistry, Faculty of Agriculture
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Yamashita K
Tohoku Univ. Sendai Jpn
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Yamamoto H
Department Of Developmental Biology And Neurosciences Graduate School Of Life Sciences Tohoku Univer
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Yamashita Kyohei
Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University
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Yamamoto Hiroshi
Department Of Energy Engineering And Science Nagoya University
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Yamamoto H
Department Of Mechanical Engineering Doshisha University
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Oritani Takayuki
Department Of Agricultural Chemistry Faculty Of Agriculture Tohoku University
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Yamamoto Hiroshi
Departmemt Of Chemical Engineering University Of Tokyo
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