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A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
(-) - 甘醇的总合成
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
概括
研究人员首次实现了 (-) - 甘醇,一种海洋毒素的总合成. 这涉及到一个融合的策略,使用木-米亚乌拉合用于核心和Stille合用于侧链.
科学领域:
- 有机化学 有机化学
- 海洋天然产品 化学 化学
背景情况:
- 海洋多环毒素对合成构成重大挑战.
- (-) 甘醇是一种复杂的海洋毒素,具有潜在的生物活性.
研究的目的:
- 为了实现第一个 (-) - 甘醇的全合成.
- 开发复杂的多环乙烯的新型合成策略.
主要方法:
- 融合合成利用木-米亚乌拉交叉合进行碎片结合.
- 通过Stille合引入敏感的三烯侧链的后期阶段.
- 使用SmI(2) 诱导的还原循环和 hetero-Michael反应,对戒指碎片进行立体选择性构造.
主要成果:
- 成功建造了 (-) - 甘醇的八环聚乙烯核心.
- 有效合成关键的ABC和EFGH环碎片.
- 通过战略合反应完成 (-) - 甘醇的总合成.
结论:
- 开发的合成途径为 (-) - 甘醇提供了一条可行的途径.
- 该研究强调了现代交叉合反应在复杂分子合成中的实用性.
- 这种合成为进一步研究 (-) - 甘醇的生物特性开辟了道路.
相关概念视频
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...

