2007 Fiscal Year Final Research Report Summary
Development of the Cyclization Reactions between Carbon-Carbon Triple Bond and Nucleophile and Its Application to the Synthesis of Biologically Active Compounds
| 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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| Keywords | Alkyne / Cyclization reaction / Heterocyclic compounds / (+)-Lysergic acid / (+)-Stephacidin A / Thunberginol A / 6Z-pandanamine / (+)-Meloscine |
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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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[Presentation] 白金触媒を用いるピロール環構築法の開発2006
Author(s)
廣谷 功, 松本 重充, 荻原 謙太郎, 芦川 正康, 坂本 尚夫
Organizer
平成18年度 化学系学協会東北大会
Place of Presentation
秋田大学手形キャンパス(秋田)
Year and Date
2006-09-23
Description
「研究成果報告書概要(和文)」より
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