1988 Fiscal Year Final Research Report Summary
Synthesis of Biologically Active Natural Products on the Basis of Silafunctional Compounds
| Project/Area Number |
61470093
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| Research Category |
Grant-in-Aid for General Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kyoto University |
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Principal Investigator |
ITO Yoshihiko Faculty of Engineering, Kyoto University, Professor, 工学部, 教授 (40026018)
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| Co-Investigator(Kenkyū-buntansha) |
HAYASHI Tamio Faculty of Engineering, Kyoto University, Instructor, 工学部, 助手 (00093295)
TAMAO Kohei Faculty of Engineering, Kyoto University, Assistant Professor, 工学部, 助教授 (60026218)
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| Project Period (FY) |
1986 – 1988
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| Keywords | Allylsilanes / Silafunctional Compounds / Stereoselective Synthesis of Polyols / ケイ素・炭素結合の酸化的切断 |
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| Research Abstract |
Synthetic methods for stereoselective preparations of polyols have been developed on the basis of silafunctional compounds, of which silicon-carbon bonds can be oxidatively cleaved and hydroxylated. The following results have been obtained.
1. Selective alpha-alkylation of (dialkylamino)allylsilanes was achieved by in-situ generation of potassium (dialkylamino)allylsilanes. Total synthesis of ( )-brevicomin was carried out viaseveral steps including the selective alpha-alkylation of (dialkylamino)allylsilane. 2. Selective deoxygenation of (isopropoxy) alpha,beta-epoxy) silanes was found in the reaction with isopropylmagnesium chloride in the presence of CuCN. 3. Stereoselective alpha-hydroxyallylation of aldehydes was achieved by in-situ generation of zinc (dialkylamino)allylsilanes. 4. Selective gamma-allylation of aldehydes was achieved by copper(I) reagents which are in-situ generated by a reaction of CuCN with lithium (dialkylamino)allylsilanes. Usefulness of the gamma-regioselective allylation of aldehydes with (dialkylamino)allylsilanes was demonstrated by synthesis of 2-deoxy-C-nucleoside skeletons.
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