Stereoselection via Intramolecular Hydrosilation
| Project/Area Number |
60550605
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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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 |
TAMAO Kohei Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University Assoc. Prof, 工学部, 助手 (60026218)
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| Project Period (FY) |
1985 – 1986
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| Project Status |
Completed (Fiscal Year 1986)
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| Budget Amount *help |
¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1986: ¥700,000 (Direct Cost: ¥700,000)
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| Keywords | Intramolecular hydrosilation / Stereocontrol / Regiocontrol / 1,3-Diol / Polyol / Biologically active natural product / Functional group transformation / 有機ケイ素化合物 |
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| Research Abstract |
This research project has been planned to develop new methodologies for regio- and stereoselective introduction of oxygen functionality to allyl and homoallyl alcohols. Intramolecular hydrosilation and subsequent oxidative cleavage of the carbon-silicon bonds have been found to proceed smoothly in many cases to give 1,3-diols in a highly regio- and stereo-selective fashion.
This new mothod has been applied to the stereoselective synthesis of racemic forms of three isomeric triols having three-consecutive chiral centers which are often found in many natural products such as polyoxy ionophores, macrolides, and ansamycins. Further transformation has afforded a tetraol having five-consecutive chiral centers, a segment of narasin, salinomycin, elaiophilin etc. Origins of the stereoselection has been discussed in terms of the reasonable transition structures. This procedure has also provided an efficient route to regioselectively mono-protected 1,3-diols from allyl and homoallyl alcohols.
Refinement and further applications to more complex natural products will be our future research project.
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Report
(1 results)
Research Products
(6 results)
