Syntheses of the sex-attractant of pine sawflies.
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概要
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In order to establish the stereochemistry of the sex attractant of various species of pine sawflies, (2<I>S</I>,3<I>R</I>,7<I>R</I>)-, (2<I>S</I>,3<I>R</I>,7<I>S</I>)- and (2<I>S</I>,3<I>S</I>,7<I>S</I>)-2-acetoxy- and 2-propionyloxy-3,7-dimethylpentadecane were synthesized. The alcohol moiety of each pheromone was prepared by the coupling of Grignard reagent of C<SUB>12</SUB> block with tosylate of C<SUB>5</SUB> block. The C<SUB>12</SUB> blocks, (<I>R</I>)- and (<I>S</I>)-1-bromo-2-methylundecane, were prepared from (<I>R</I>)-(+)-pulegone. The C<SUB>5</SUB> blocks, (2<I>R</I>,3<I>S</I>)- or (2<I>S</I>,3<I>S</I>)-2-methyl-3-tetrahydropyranyloxy-1-(tosyloxy)butane, were derived from (2<I>S</I>,3<I>S</I>)- or (2<I>R</I>,3<I>S</I>)-2-methyl-3-hydroxybutyric acid prepared by the enantio-differentiating hydrogenation of methyl 2-methyl-3-oxobutyrate over the asymmetrically modified nickle catalyst.
- 公益社団法人 日本化学会の論文
著者
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Tai Akira
Institute For Protein Research Osaka University
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Imaida Motomasa
Institute for Protein Research, Osaka University
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Kikukawa Tadashi
Institute for Protein Research, Osaka University
関連論文
- Affinity Chromatography of a Group Specific Adsorbent for Pyridoxal Phosphate Dependent Enzymes(Biological Chemistry)
- The preparation of optically pure 3-hydroxyalkanoic acid. The enantioface-differentiating hydrogenation of the C=O double bond with modified Raney nickel. XXXVII.
- The enantioface-differentiating hydrogenation of the C=O double bond with asymmetrically modified raney nickel. XXXIII. The preparation of (R)- and (S)-1,3-butanediol from 4-hydroxy-2-butanone.
- Stereochemical studies of the hydrogenation with asymmetrically modified nickel catalysts; the hydrogenation of methyl 2-alkyl-3-oxobutyrate.
- Syntheses of the sex-attractant of pine sawflies.
- The stereo-differentiating (asymmetric) hydrogenation of the C=O double bond with a modified nickel catalyst. XXXV. A facile method for the preparation of optically pure .BETA.-diols.
- Stereochemical studies of the hydrogenation with an asymmetrically modified Raney nickel catalyst. The hydrogenation of acetylacetone.
- Stereochemical investigation on asymmetrically modified Raney nickel catalyst. Mode of interaction between modifying reagent and substrate in the enantioface-differentiating process.