| Project/Area Number |
18390001
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Tohoku University |
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Principal Investigator |
SAKAMOTO Takao Tohoku University, Professor Emeritus (00006347)
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| Co-Investigator(Kenkyū-buntansha) |
HIROYA Kou Tohoku University, Graduate School of Pharmaceutical Sciences, Associate Professor (70192721)
INAMOTO Kiyofumi Tohoku University, Graduate School of Pharmaceutical Sciences, Assistant Professor (30359533)
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| Project Period (FY) |
2006 – 2007
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| Project Status |
Completed (Fiscal Year 2007)
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| Budget Amount *help |
¥16,600,000 (Direct Cost: ¥14,800,000、Indirect Cost: ¥1,800,000)
Fiscal Year 2007: ¥7,800,000 (Direct Cost: ¥6,000,000、Indirect Cost: ¥1,800,000)
Fiscal Year 2006: ¥8,800,000 (Direct Cost: ¥8,800,000)
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| Keywords | Alkyne / Cyclization reaction / Heterocyclic compounds / (+)-Lysergic acid / (+)-Stephacidin A / Thunberginol A / 6Z-pandanamine / (+)-Meloscine / Platinum(IV) chloride / Platinum(II) chloride / Pyrrole / Isocoumarin / Phthalide / Thunberginol |
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| Research Abstract |
The first object of this research is establishment of the general synthetic method for heterocyclic compound by the cyclization reaction between carbon-carbon triple bond and nucleophile containing heteroatom as a key reaction. The second and third objects are investigation of the reaction mechanism for Pd-catalyzed cyclization reaction and application of this methodology to the synthesis of the biologically active heterocyclic compounds. Consequently, the following results could be obtained during the term of the project.
1. The optimization of the reaction condition for the cyclization of 2-ethynylaniline derivatives to indoles catalyzed by PD(0)-methyl propiolate together with the scope and limitation of this reaction were investigated.
2. The real catalytic species of the above catalytic reaction were elucidated by spectroscopic methods.
3. New method for the synthesis of multi-substituted pyrrole ring system catalyzed by platinum complex could be established.
4. The relationship between the reactivity and the regioselectivity for the cyclization reactions of 2-en-4-yne carboxylic acid derivatives was investigated.
5. The synthetic method for the BC ring system of (+)-lysergic acid was established by sequential cyclization reaction of 2-ethynylaniline dervative using C8(II)salt.
6. The BCDFG ring system of (+)-stephacidin A could be synthesized as an optically active form.
7. Synthetic studies for (-)-rhazinilam and (+)-meloscine were investigated.
8. The total synthesis of thunbergiol A, B and 6Z-pandanamine were accomplished by acid or base promoted cyclization reactions of 2-en-4-yne carboxylic acid derivatives.
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