2001 Fiscal Year Final Research Report Summary
Development of New Methodologies for the efficient synthesis of biologically active compounds
| Project/Area Number |
12660101
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Bioproduction chemistry/Bioorganic chemistry
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| Research Institution | Osaka Prefecture Unicersity |
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Principal Investigator |
TANIMORI Shinji Graduate School of Agriculture and Biological Sciences, Osaka Prefecture University, Associate Professor, 農学生命科学研究科, 助教授 (50207198)
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| Co-Investigator(Kenkyū-buntansha) |
KIRIHATA Mitsunori Graduate School of Agriculture and Biological Sciences, Osaka Prefecture University, Professor, 農学生命科学研究科, 教授 (60128767)
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| Project Period (FY) |
2000 – 2001
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| Keywords | oxazolidone / palladium catalyst / allylic substitution / cyclic ADP-ribose / asperparaline / Jasmonic acid / indolidine alkaloid / asymmetric synthesis |
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| Research Abstract |
1. Development of transition metal-catalyzed tandem organi reaction
Reaction of 2-butenylene dicarbonate with primary amine was catalyzed by palladium-phosphine catalyst to produce novel 5-vinyl oxazolidone in good yield. Asymmetric induction of this reaction was achieved by using chiral bidentate phosphine ligand to produce chiral oxazolidone derivatives in 90 % enantio selectivity.
2. Synthetic approach for both enantiomars of jasmonic acid
Reaction of meso-1, 4-diacetoxycyclopentene with dimethyl malonate in the presence of palladium-chiral phosphine catalyst possessing C_2-symmetry to give alkylated product in 85 % enentiomeric purity. The product was converted into knouw intermedate for the synthesis of jasmonic acid.
3. Synthetic approach for asperparaline, an indolidine alkaloid posessing potent Paralytic activity
Enyne derived from praline was subjected to Pauson-Khand cycloaddition using cobalt octacarbonyl to produce tricyclic indolidine, which was treated with methylamine to gibe teracyclic bridged amide, a potential intermediated for asperparaline C in good yield.
4 Synthetic approach for cyclic ADP-ribose, a second messenger for Ca^<2+> release
Efficient chemical synthesis of NMN and derivatives, a precursor of NAD, was developed Reaction of tetraacetate prepared fron D-ribose with nicotinamide in the presence of Lewis acid (TMSOTf) followed by treatment of methanol to provide NAR, which was phopholylated to give desired NMN in good yield.
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