関連する実験動画
Updated: Jul 13, 2026

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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
(-) -ガンビエロールの合成総量
Haruhiko Fuwa1, Noriko Kainuma, Kazuo Tachibana
1Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Journal of the American Chemical Society
|December 12, 2002
まとめ
研究者らは,海洋毒素である (-) - ガンビエロルの最初の完全な合成を達成しました. これには,コアにスズキ-ミヤウラカップリング,サイドチェーンにスティルカップリングを用いたコンバージェント戦略が必要でした.
科学分野:
- 有機化学 オーガニック・ケミストリー
- 海洋自然産物 化学 化学
背景:
- 海洋ポリサイクルエーテル毒素は,重要な合成課題を提起しています.
- (-) -ガンビエロールは,潜在的な生物学的活性を持つ複雑な海洋毒素です.
研究 の 目的:
- (-) -ガンビエロルの最初の完全合成を達成するために.
- 複雑なポリサイクルエーテルのための新しい合成戦略を開発する.
主な方法:
- 断片結合のためのスズキ-ミヤウラクロスカップリングを用いた収束合成.
- Stille カップリングによる敏感なトリエンのサイドチェーンの後期導入.
- SmI(2) 誘発の還元サイクルとヘテロマイケルの反応を用いてリングの断片をステレオ選択的に構築する.
主要な成果:
- (-) -ガンビアロールのオクタサイクリックポリエーテルコアの建設が成功しました.
- 主要なABCとEFGHリングの断片を効率的に合成する.
- 戦略的結合反応を通じた (-) -ガンビエロールの全合成の完了.
結論:
- 開発された合成経路は, (-) -ガンビエロールへの有効な経路を提供します.
- この研究は,複雑な分子合成における現代のクロスカップリング反応の有用性を強調しています.
- この合成により, (-) - ガンビエロルの生物学的性質をさらに調査する道が開かれました.
関連する概念動画
Organic Compounds
All living things are formed mostly of carbon compounds called organic compounds. The category of organic compounds includes both natural and synthetic compounds that contain carbon. Although a single, precise definition has yet to be identified by the chemistry community, most agree that a defining trait of organic molecules is the presence of carbon as the principal element, bonded to hydrogen and other carbon atoms. However, some carbon-containing compounds such as carbonates, cyanides, and...
Acidity and Basicity of Alcohols and Phenols
Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Carboxylic Acid Derivatives: Overview
Carboxylic acid derivatives are formed by replacing the hydroxyl group of carboxylic acids with a different functional group. The most common carboxylic acid derivatives are:
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides
Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
Structures of Carboxylic Acid Derivatives
Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...
Structures of Aldehydes and Ketones
Vanillin—a flavoring agent in vanilla, cinnamaldehyde—a molecule responsible for the distinct smell of cinnamon, and acetone—a strong-smelling ingredient in nail polish removers, all belong to a class of carbonyl compounds called aldehydes and ketones (Figure 1). Although both aldehydes and ketones contain the characteristic carbonyl (C=O) bond, their chemical structures vary with respect to the groups directly attached to the carbonyl carbon.
In aldehydes (Figures 1a and 1b), the carbonyl...
In aldehydes (Figures 1a and 1b), the carbonyl...

