聚烯循环/曼尼克级联为简化构建的A/E/F三环系统的迪特尔类化物
Yueshen Feng1, Shuping Li1, Minhang Chang1
1Shaanxi Key Laboratory of Natural Products and Chemical Biology, College of Chemistry and Pharmacy, Northwest A&F University, 3 Taicheng Road, Yangling, Shaanxi Province 712100, China.
Organic letters
|June 19, 2025
概括
研究人员用一种新的聚烯循环和曼尼赫级联来合成复杂的三环二类化物. 这种方法有效地创建了特征性的A/E/F环系统,具有特特的立体化学特征.
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
- 药用化学 医学化学
背景情况:
- 包括C18,C19和denudatine类型在内的迪特尔类类化合物具有复杂的多环结构.
- 在这些具有生物学意义的自然产品中,A/E/F三环系统是关键的结构图案.
- 获得这些复杂的支架的高效合成路线对于进一步的研究至关重要.
研究的目的:
- 开发一种新的合成策略,用于构建在二类类化合物中发现的A/E/F三环系统.
- 在合成过程中实现立体选择性控制,特别是对于基导向.
- 建立适用于C18,C19和denudatine类型类化合物合成的多功能方法.
主要方法:
- 一个经过战略设计的聚烯循环反应,其次是曼尼赫级联反应.
- 在C7位置使用了激进级联过程来进行配置反转.
- 包含序列的1,5-原子转移 (HAT) 和分子间HAT反应.
主要成果:
- 成功构建了特征性的A/E/F三环系统的二类类化合物.
- 通过激素级联,通过C7实现了基组的配置反转.
- 通过面向β的基组建立了所需的三环系统,证明了高立体选择性.
结论:
- 开发的聚烯循环/曼尼克级联为复杂的三环四类类化合物提供了一条有效的途径.
- 激素级联策略使精确的立体化学控制成为可能,这对于天然产品合成至关重要.
- 这种方法为合成各种C18,C19和denudatine类型化物奠定了基础.
相关概念视频
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
4.2K
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.
4.2K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
4.8K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.8K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
10.8K
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.
10.8K
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization
2.6K
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
2.6K
Cycloaddition Reactions: Overview
2.8K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.8K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K

![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)
