立体分离的乙烯甲基Z的总合成
Nicolas Jamey1, Laurent Ferrié1
1BioCIS, Faculté de Pharmacie, Université Paris-Saclay, CNRS, 91400 Orsay France.
Organic letters
|June 27, 2024
概括
研究人员首次实现了海洋内氧化物乙烯甲酸Z的全合成. 本研究提出了一种高效的11步策略,用于合成这一重要类化合物.
科学领域:
- 海洋天然产品化学 海洋天然产品化学
- 有机合成 有机合成
- 药品化学 药品化学 是一个
背景情况:
- 皮质是海洋内氧化物,具有多种生物活性.
- 乙烯甲酸Z,其简单的侧链,是合成策略的关键目标.
研究的目的:
- 开发和展示一个普适的合成策略,用于 plakortides.
- 为了实现第一个乙烯甲酸的全合成,Z.
主要方法:
- 非对称 终止化.
- 区域选择性循环butanol氧化扩张.
- 过氧碳离子介导的C-C键形成.
- 准备性高性能液体染色学 (HPLC) 用于二聚体分离.
主要成果:
- 在11个步骤中成功合成乙烯甲酸Z.
- 在总合成中获得了4.2%的整体收益率.
- 证明了开发的合成策略的可行性.
结论:
- 完成了第一个乙烯甲酸Z的全合成.
- 开发的策略是高效的,适用于 plakortide 子家族.
- 这项工作为进一步探索板酸衍生物提供了基础.
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
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
Stereoisomers
12.7K
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...
12.7K
Polymer Classification: Stereospecificity
2.4K
Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...
2.4K
Stereoisomerism of Cyclic Compounds
8.8K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
8.8K
E2 Reaction: Stereochemistry and Regiochemistry
11.5K
Elimination reactions of alkyl halides can yield one or more alkenes depending on the specific regiochemical and stereochemical considerations. While the regiochemistry of the reaction governs the location of the double bond in the product, the stereochemical requirements often influence the geometry.
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
When a substrate with two different β hydrogens undergoes an E2 elimination, the presence of a strong base can yield two regioisomeric alkenes. The more-substituted alkene is the major...
11.5K

![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
