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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
12.4K
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

4.0K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
4.0K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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.
3.3K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

12.0K
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.
12.0K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.6K
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.
4.6K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.5K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the para...
3.5K

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Diagonal Method to Measure Synergy Among Any Number of Drugs
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(+) - 桑帕诺利德和 (+) - 达克提洛利德的总合成利用统一的战略.

Amos B Smith1, Igor G Safonov, R Michael Corbett

  • 1Contribution from the Department of Chemistry, Monell Chemical Senses Center, and Laboratory for Research on the Structure of Matter, University of Pennsylvania, Philadelphia, Pennsylvania 19104. smithab@sas.upenn.edu

Journal of the American Chemical Society
|September 13, 2002
PubMed
概括

研究人员首次实现 (+) - 桑帕诺利德和 (+) - 达克提洛利德的总合成,这两种新型宏类药物抑制瘤细胞生长. 这些合成使用了对关键结构特征的立体控制方法,推进了癌症研究.

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科学领域:

  • 有机化学 有机化学
  • 药用化学 医学化学
  • 化学合成 化学合成

背景情况:

  • 赞帕诺利德和达克提洛利德代表了一种新的宏类,具有已证明的瘤细胞生长抑制特性.
  • 这些天然产品的复杂结构带来了重大的合成挑战.

研究的目的:

  • 为了实现 (+) - 桑帕诺利德和 (+) - 达克提洛利德的第一个全合成.
  • 为这些相关的宏类化合物制定统一的合成策略.
  • 为了分配合成化合物的完整的相对和绝对立体化学.

主要方法:

  • 采用了一种统一的合成方案,采用修改后的Petasis-Ferrier重新排列,用于立体控制的四基结构.
  • 为了组装宏循环核心,使用了融合策略.
  • 对于赞帕诺利德,使用了库尔蒂乌斯重组/化序列,以安装N-酸 hemiaminal部分.

主要成果:

  • 首次成功完成 (+) - 赞帕诺利德和 (+) - 达克提洛利德的总合成.
  • 合成策略的关键要素是对cis-2,6-非替代四胺基的立体控制构造.
  • 分配了两个天然产品的相对和绝对立体化学,并对 (+) - 桑帕诺利德进行了初步分配.

结论:

  • 开发的合成途径提供了获得新型瘤细胞生长抑制剂的途径.
  • 成功的合成验证了拟议的立体化学赋值,并证明了所采用的合成方法的实用性.
  • 这项工作为进一步研究这些宏类体的生物活动和结构类比铺平了道路.