Synthetic study of indolalkaloids using a [3+3] cycloaddition reaction
| Project/Area Number |
25460019
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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 |
Kato Nobuki 名古屋市立大学, 薬学研究科(研究院), 講師 (50400221)
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| Project Period (FY) |
2013-04-01 – 2016-03-31
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| Project Status |
Completed (Fiscal Year 2015)
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| Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
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| Keywords | インドールアルカロイド / 分子内酸化的カップリング / かご型構造 / 有機合成 / 環化付加反応 |
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| Outline of Final Research Achievements |
Scholarisine A, isolated from the leaves of Alstonia scholaris, is a monoterpene indole alkaloid with an unprecedented cage-like structure. In this paper, preparation of the distinctive cage-like core skelton of the Scholarisine A is described. The key feature of this synthetic strategy is an intramolecular oxidative coupling reaction at the late stage to construct a 10-oxa-tricyclo[5.3.1.03,8]undecan-9-one structure fused with indolenine. Intramolecular oxidative coupling using N-iodosuccinimide gave the carbon framework of Scholarisine A in moderate yield, which is the first example of intrarmolecular oxidative coupling reaction between non-activated enolate and indole. This study lays the foundation for continued investigations toward the total synthesis of Scholarisine A.
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Report
(4 results)
Research Products
(15 results)
