Asymmetric Synthesis Using Chiral Acetals : Highly Stereoselective Reduction of Chiral α-Keto-β, γ-unsaturated Acetals and Its Application for the Synthesis of (R)-(-)- and (S)-(+)-3'-Methoxy-4'-O-methyljoubertiamine
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概要
- 論文の詳細を見る
Reduction of the chiral α-keto-β, γ-unsaturated acetals (1) derived from (-)-(2S, 3S)-1,4-dimethoxy-2,3-butanediol was studied. Extremely high stereoselectivity was attained with LiAlH_4 and two epimeric allyl alcohols (2aA-2cA and 2aB-2cB) were prepared selectively by a proper choice of additive. As an application of this methodology, total syntheses of (R)-(-)-3'-methoxy-4'-O-methyljoubertiamine [(R)-(-)-4] and its enantiomer [(S)-(+)-4] were achieved from the single chiral enone acetal (3) through a highly stereocontrolled reduction followed by the Claisen-Eschenmoser rearrangement.
- 社団法人日本薬学会の論文
- 1989-08-25
著者
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田村 恭光
Faculty Of Pharmaceutical Sciences Osaka University
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北 泰行
Faculty of Pharmaceutical Sciences, Osaka University
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北 泰行
大阪大学大学院薬学研究科
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藤岡 弘道
大阪大学大学院薬学研究科
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藤岡 弘道
Faculty Of Pharmaceutical Sciences Osaka University
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Kita Yasuyuki
Graduate School Of Pharmaceutical Sciences Osaka University Yamadaoka
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案浦 洋一
Faculty of Pharmaceutical Sciences, Osaka University
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村埜 賢司
Faculty of Pharmaceutical Sciences, Osaka University
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村埜 賢司
Faculty Of Pharmaceutical Sciences Osaka University
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案浦 洋一
Faculty Of Pharmaceutical Sciences Osaka University
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北 泰行
Faculty Of Pharmaceutical Sciences Osaka University
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