1987 Fiscal Year Final Research Report Summary
Facile Synthesis of Bioactive Amino Alcohols Utilizing 2-Oxazolone Heterocycle
| Project/Area Number |
60470150
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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 |
Chemical pharmacy
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| Research Institution | Kumamoto University |
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Principal Investigator |
KUNIEDA Takehisa Faculty of Pharmaceutical Sciences, Kumamoto University, 薬学部, 教授 (80012649)
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| Co-Investigator(Kenkyū-buntansha) |
ISHIZUKA Todao Faculty of Pharmaceutical Sciences, Kumamoto University, 薬学部, 教務員 (60176203)
NAGAMATSU Tomohisa Faculty of Pharmaceutical Aciences, Kumamoto University, 薬学部, 助手 (40155966)
SAKUMA Yoshiharu Faculty of Pharmaceutical Sciences, Kumamoto University, 薬学部, 助教授 (70040318)
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| Project Period (FY) |
1985 – 1987
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| Keywords | 2-Oxazolone / Chiral synthon / Amino alcohol / Statine / Hydroxy-glutamic acid / Beta-Latam / Mixed phosphotriester / 合成試薬 |
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| Research Abstract |
Much synthetic potential of 4,5-unsubstituted 2-oxazolone heterocycle has been explored as a versatile builbing block for vic-amino alcohol structures found in a number of biosctive compounds as well as promising leaving moiety if carboxyl and phosphoryl activation processes.
1. Chiral Synthons for 1,2-Amino Alcohols : Good verrsatile strategy from such a simple heterocycle to a wide variety of 1,2-amino alcohols has been developed by highyl regio and stereoselective preparation of chiral synthons, 4-methoxy-5-bromo-2-oxazolidinones, followed by stereospecific and stepwise substitution reactions. This methodology is shown highly promising for the efficient preparation of biologically significant hydroxy smino scids such as 4-amino-3-hydroxy-6-methylheptanoic acid (statine), 3-hydroxy-glutamic acid and 4-amino-3- hydroxylutyric acid (GABOB).
2. New Synthetic Reagents : The oxazolone-based compounds, aryl bis(2-oxo-3-oxazolinyl) phosphinate and tris(2-oxo-3-oxazolinyl)phosphine oxide, have been newly introduced as excellent reagents for phosphorylation mild enough to benefit fields ranging from phospholipids to polynucleotides and for <bata>-lactam formation from <bata>-amino acids including a facile preparation of the penam, a basic skeleton of penicillins.
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