相关实验视频
Updated: Jul 12, 2026

14:18
A Strategy for Sensitive, Large Scale Quantitative Metabolomics
Published on: May 27, 2014
总合成 (+/-) -二甲基二氨酸 (阿斯巴拉加胺A) 和 (+/-) -二甲基二氨酸
Markus Brüggemann1, Andrew I McDonald, Larry E Overman
1Department of Chemistry, 516 Rowland Hall, University of California, Irvine, CA 92697-2025, USA.
Journal of the American Chemical Society
|December 11, 2003
概括
实现了第一个didehydrostemofoline和isodidehydrostemofoline的总合成. 关键步骤包括迪尔斯-阿尔德反应和阿扎-科普-马尼奇反应,以构建复杂的分子框架.
科学领域:
- 有机化学 有机化学
- 合成化学 合成化学
- 药用化学 医学化学
背景情况:
- 斯特莫福林是一种复杂的化物,具有潜在的生物活性.
- 对于进一步的研究,高效的合成途径到stemofoline类似物至关重要.
研究的目的:
- 报告 (+/-) - - 滴滴水质提摩林和 (+/-) - - 滴滴水质提摩林的第一个总合成.
- 为这些具有挑战性的分子目标建立可靠的合成途径.
主要方法:
- 合成始于醇和乙烯 (E) -3-基酸盐之间的迪尔斯-阿尔德反应.
- 关键的中间体,包括7-azabicyclo[2.2.1]heptanol和1-azatricyclo[5.3.0.04.10]decane,通过化和Aza-Cope-Mannich反应形成.
- 随后的15步序列完成了目标分子的合成.
主要成果:
- 完成了成功的和第一次的 (+/-) -didehydrostemofoline (1) 和 (+/-) -isodidehydrostemofoline (3) 的总合成.
- 合成策略有效地构建了目标化物复杂的多环核结构.
- 迪尔斯-阿尔德和阿扎-科普-曼尼奇反应在组装分子框架方面发挥了关键作用.
结论:
- 开发的合成途径提供了didehydrostemofoline和isodidehydrostemofoline的获取.
- 这项工作奠定了探索生物性质的基础,并开发了stemofoline类化合物的类似物.
- 报告的合成表明了复杂分子结构中战略循环加和重排反应的力量.
相关概念视频
Brønsted-Lowry Acids and Bases
In 1923, the Brønsted–Lowry definition of acids and bases was proposed by Johannes Brønsted and Thomas Lowry. According to this theory, a Brønsted acid is defined as a species that donates a proton in a chemical reaction and gets converted to its conjugate base. A Brønsted base is defined as a species that accepts a proton in a chemical reaction and gets converted into its conjugate acid. These transfers of protons are caused by the displacement of electrons in these reactions, which is...
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.
Base-Catalyzed Aldol Addition Reaction
As depicted in Figure 1, base-catalyzed aldol addition involves adding two carbonyl compounds in aqueous sodium hydroxide to form a β-hydroxy carbonyl compound.
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds
α,β-Unsaturated carbonyl compounds are molecules bearing a carbonyl and alkene functionality in conjugation with each other. The conjugation in the molecule leads to three resonance structures. The hybrid form exhibits two probable electrophilic sites: the carbonyl carbon and the β carbon.
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Solution Composition During Acid/Base Titrations
The titration of a weak acid with a strong base results in the formation of water and the conjugate base of the acid. For instance, titrating acetic acid with sodium hydroxide leads to the formation of water and sodium acetate. A solution of acetic acid and sodium acetate constitutes a buffer whose relative concentration at different stages of the titration is indicated by the α values, which represent percentages of the weak acid and its conjugate base.
The α0 and α1 values represent the...
The α0 and α1 values represent the...

