1994 Fiscal Year Final Research Report Summary
Development of practical synthetic method for preparation of alcohols in chiral from.
| Project/Area Number |
05650871
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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 | Tokyo Institute of Technology |
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Principal Investigator |
SATO Fumie T.I.T., Biosci.&Biotech., Professor, 生命理工学部, 教授 (50016606)
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| Project Period (FY) |
1993 – 1994
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| Keywords | Asymmetric Synthesis / Asymmetric epoxidation / Asymmetric dihydroxylation / Allyl Alcohol / Butyrolactone / Chiral building block / Hydromagnesiation Reaction / Allylsilane |
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| Research Abstract |
If biologically active compounds have asymmetric center, the two enantiomers, usually, show differnent biological activities. Thus it has been required to develop one enantiomer, not racemic compound, as drugs or agricalutural chemicals. The development of practical method which can be viable in indurially scale production, therefore, has been the important subject in organic synthesis. The purpose of the present research is the development of efficient and practical method for synthesis of alcohols in optically pure from. Since alcohols are embeded in various kinds of biologically active substances and also have been widely accepted as useful intermediates for synthesis of natural compounds, the practical synthetic methodolgy for preparation of optically active alcohols has been strongly anticipated.
The Sharpless asymmetric dihydroxylation of allyl silane followed by the Petterson reaction provided optically active allyl alcohols in excellent yields. The Sharpless asymmetric dihydroxylation of enyne gave propargylic alcohols having another hydroxyl group at beta-position. Hydromagnesiation of these diols followed by treatment with aldehyde or CO_2 provided furyl alcohols or butenolides, respectively, in a chiral form. By using these chiral alcohols as chiral building block, a few biological compounds were synthesized.
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