Studies on the chemical synthesis of antitumor saponins for the evaluation of their biological activities
| Project/Area Number |
23590014
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Nagoya City University |
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Principal Investigator |
SEIICHI NAKAMURA 名古屋市立大学, 薬学研究科(研究院), 教授 (90261320)
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| Project Period (FY) |
2011 – 2013
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| Project Status |
Completed (Fiscal Year 2013)
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| Budget Amount *help |
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2013: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2012: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2011: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
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| Keywords | シラシロシド類 / 抗腫瘍性サポニン / Ireland－Claisen転位 / 二連続第四級不斉中心 / ニトリルオキシド / 1,3-双極付加環化 / シクロプロパン化 / 酸化型ジテルペノイド / シラシロシドE-1 / サポニン / 抗腫瘍活性 / Lebelオレフィン化 / α-ジアゾ-β-ケトエステル / 分子内O-H挿入反応 / Ireland-Claisen転位 / いす形遷移状態 / C20位メチル基 |
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| Research Abstract |
Toward the total synthesis of antitumor saponins scillascillosides, the stereoselective construction of CDE ring system of these molecules have been explored. Ireland-Claisen rearrangement of the dihydrofurancarboxylate, obtained by intramolecular O-H insertion followed by olefination, proceeded stereoselectively to give the desired stereoisomer in good yield. The product was successfully converted to the CDE ring fragment through an intramolecular 1,3-dipolar cycloaddition and introduction of an angular methyl group. With regard to the key Ireland-Claisen rearrangement, we found that the substitution pattern of the adjacent carbon atom played a pivotal role in directing the stereochemical course of the reaction, and this finding led to the development of methods for the stereodivergent syntheses of two chiral building blocks.
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Report
(4 results)
Research Products
(18 results)
