Facile construction of optically active 1,3-diols. Synthesis of (2S,4R)-7-octene-2,4-diol and endo-(1S,3S,5R)- and exo-(1R,3S,5S)-1,3-dimethyl-2,9-dioxabicyclo[3.3.1]nonane.
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概要
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A short and stereoselective asymmetric synthesis of (2<I>S</I>,4<I>R</I>)-7-octene-2,4-diol (a key intermediate in the Bartlett synthesis of nonactic acid) and two stereoisomers of a biologically active substance isolated from Norway spruce infested by ambrosia beetle, <I>endo</I>-(1<I>S</I>,3<I>S</I>,5<I>R</I>)- and <I>exo</I>-(1<I>R</I>,3<I>S</I>,5<I>S</I>)-1,3-dimethyl-2,9-dioxabicyclo-[3.3.1]nonane, was effectively accomplished in three and four reaction steps, respectively, by starting with easily obtainable (<I>S</I>)-1-(1,3-dithian-2-yl)-2-propanol by baker's yeast asymmetric reduction. The main strategy was based on a facile construction of optically active β-hydroxy ketones via alkylation of the dianion of (<I>S</I>)-1-(1,3-dithian-2-yl)-2-propanol with alkyl halides, followed by their stereoselective reductions.
著者
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Chikashita Hidenori
Department Of Applied Chemistry Faculty Of Engineering Kansai University
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Kimura Yasunori
Department Of Mathematical And Computing Sciences Tokyo Institute Of Technology
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Itoh Kazuyoshi
Department Of Applied Chemistry Faculty Of Engineering & High Technology Research Center Kansai
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Kittaka Eiji
Department of Applied Chemistry, Faculty of Engineering, Kansai University
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