(-) - 皮埃里康 D 的总合成
Shaopan Yuan1,2, Wanqing Pei1,2, Xuan Di1
1School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China.
The Journal of organic chemistry
|May 31, 2024
概括
实现了 (-) - 皮埃里康 D 的总合成,这是一种潜在的抗血栓剂. 这种二甲基具有独特的[3.3.0] 八度核,使得进一步的结构-活性关系研究成为可能.
科学领域:
- 有机化学 有机化学
- 药用化学 医学化学
- 自然产品的合成自然产品的合成
背景情况:
- (-) - 皮埃里康 D 是一种具有潜在抗血栓活性的二甲基.
- 它的复杂结构,包括一个 [3.3.0] 度的核心,提出了一个合成的挑战.
研究的目的:
- 报告第一个 (-) - 皮埃里康 D. 的总合成.
- 开发一种可接受结构-活性关系 (SAR) 研究的融合合成路径.
主要方法:
- 立体选择性β-O-糖化,以附加阿塞博根因糖.
- 晚期的全球降低保护和同时的乳化.
- 收的合成策略.
主要成果:
- 成功的 (-) - 皮埃里康 D 的总合成.
- 展示关键的立体选择和后期转换.
- 为SAR调查建立一个可行的路线.
结论:
- 成功完成了 (-) - - 皮埃里康D 的总合成.
- 开发的合成策略为进一步的生物评估提供了对 (-) - 皮埃里康D的访问.
- 这项工作促进了未来的SAR研究,以优化抗血栓潜力.
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
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)
1.0K
When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
1.0K
[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
Sharpless Epoxidation
4.0K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
4.0K
Preparation of Epoxides
7.6K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
7.6K


