达尔迪南的合成及其亚tropisomers的动态立体化学
Hitoshi Kamauchi1, Miki Goto1, Yoshiaki Sugita1
1Department of Pharmaceutical Sciences, Faculty of Pharmacy and Pharmaceutical Sciences, Josai University, 1-1 Keyaki-dai, Sakado, Saitama 350-0295, Japan.
The Journal of organic chemistry
|June 11, 2024
概括
研究人员合成了daldinans B和E,这是Daldinia concentrica的天然产品. 形状分析揭示了体,旋转在C-3-C-8轴周围解释了这一现象.
科学领域:
- 有机化学 有机化学
- 自然产品的合成自然产品的合成
- 计算化学计算化学
背景情况:
- Daldinia concentrica是一种已知产生生物活性二次代谢产物的真菌.
- 类型:Isoindolinones 是一类含有的异环化合物,具有多种生物活性.
- 基体是由于围绕单一键的旋转受到阻碍而产生的立体体体.
研究的目的:
- 为了实现达尔迪南B和E的合成,它们是3-异印丁.
- 为了研究这些合成的isoindolinones的结构性质和atropisomerism.
- 为了阐明观察到的体化过程的机制和能量屏障.
主要方法:
- 达尔迪南B和E的总合成.
- 使用衍生品对形状性质的分析.
- 可变温度核磁共振 (VT-NMR) 光谱学.
- 密度函数理论 (DFT) 的计算.
主要成果:
- 成功合成达尔迪南B和E (化合物5和8).
- 在isoindolinone衍生物中鉴定和表征基体.
- 使用VT-NMR.估计激活自由能障碍物用于化.
- DFT的计算证实,阻碍 C-3-C-8 轴周围的旋转是化原因.
结论:
- 达尔迪南B和E的合成为进一步研究提供了这些天然产品的获取.
- 构造分析证实了这些3 - - 类单体中存在稳定的基体.
- 通过在C-3-C-8键周围的缓慢旋转,通过可量化的能量屏障,发生了化.
相关概念视频
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
3.9K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.9K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.1K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
4.6K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.6K
Diels–Alder Reaction: Characteristics of Dienes
4.1K
The Diels–Alder reaction brings together a diene and a dienophile to form a six-membered ring. Both components have unique characteristics that influence the rate of the reaction.
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
Characteristics of the diene
Conformation
The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is...
4.1K
Stereoisomers
12.8K
On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...
12.8K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
2.7K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.7K


