Natural Product Synthesis Based on New Methods for Constructing Quaternary Stereogenic Carbon Atoms
| Project/Area Number |
18H01970
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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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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Hokkaido University |
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Principal Investigator |
TANINO Keiji 北海道大学, 理学研究院, 教授 (40217146)
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| Project Period (FY) |
2018-04-01 – 2021-03-31
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| Project Status |
Completed (Fiscal Year 2020)
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| Budget Amount *help |
¥16,900,000 (Direct Cost: ¥13,000,000、Indirect Cost: ¥3,900,000)
Fiscal Year 2020: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2019: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2018: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
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| Keywords | 合成化学 / 四級炭素 / 転位反応 / 天然物合成 / 第四級不斉炭素 / 高次構造天然物 / 全合成 |
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| Outline of Final Research Achievements |
A new method for stereoselective construction of a quaternary stereogenic carbon atom was developed based on a formal rearrangement reaction of epoxy cyanoalcohols. The utility of the new method was demonstrated through the concise total synthesis of verrucarol, the saponification product of the macrocyclic fungal metabolite verrucarin J.
On the other hand, total synthesis of Hispidospermidin, a natural product possessing a unique caged skeleton, was accomplished based on a two-step transformation of a ketone into a gem-divinyl compound by a rearrangement reaction.
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| Academic Significance and Societal Importance of the Research Achievements |
天然物の全合成研究は、新しい合成手法の開発を促し、有機化学の飛躍的な発展をもたらしてきた。その意義は単に学術面に留まらず、医薬や農薬の創出など社会的な要請にも応えるものである。
本研究では、独自に設計した「エポキシニトリルの形式的転位反応」および「転位反応によるgem-ジビニル化合物の高効率合成」を用いて、従来困難とされてきた第四級不斉炭素の立体選択的かつ効率的な構築法を開発した。また、それら新手法の有用性を、天然物ベルカロールおよびヒスピドスペルミジンの短段階全合成において実証した。
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Report
(4 results)
Research Products
(16 results)
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[Journal Article] Development of a 1,3a,6a-Triazapentalene Derivative as a Compact and Thiol-specific Fluorescent Labeling Reagent2020
Author(s)
Atsushi Nakayama, Akira Otani, Tsubasa Inokuma, Daisuke Tsuji, Haruka Mukaiyama, Akira Nakayama, Kohji Itoh, Akira Otaka, Keiji Tanino, and Kosuke Namba
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Journal Title
Communications Chemistry
Volume: 3
Issue: 1
Pages: 1-9
DOI
NAID
Related Report
Peer Reviewed / Open Access
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