保护 (-) - - 兰诺丁丁B的无组总合成
Hui Ming Ge1, Lan-De Zhang, Ren Xiang Tan
1State Key Laboratory of Coordination Chemistry, Nanjing National Laboratory of Microstructures, Institute of Chemical Biology and Drug Innovation, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
Journal of the American Chemical Society
|July 18, 2012
概括
作为Lycopodium annotinum成分的 (-) - 兰诺丁丁B的首次全合成是在10个步骤中实现的. 这种高效的合成采用了新的还原性氨基化和乙烯凝结方法.
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:
- 莱科波 (Lycopodium annotinum) 含有独特的四环类化物.
- (-) - - 兰诺丁丁B是一种复杂的天然产品,具有潜在的生物活性.
- 以前的合成途径到类似的化合物是漫长的或低收益的.
研究的目的:
- 为了实现第一个 (-) - 兰诺丁丁B的全合成,B.
- 制定一个简洁而高效的合成策略.
- 探索用于构建复杂化物框架的新型化学转换.
主要方法:
- 设计了一个10步合成序列.
- 关键步骤包括化疗和立体选择性降解性氨基化.
- 对于环坦的形成,采用了分子内乙烯凝结.
- 使用了一种保护无组策略.
主要成果:
- (-) - - 兰诺丁丁B的总合成成功完成.
- 实现了23%的整体收益率.
- 合成建立了一个转的6/6自行车和一个7个成员的环.
- 确定了一个最佳的氧化还原顺序.
结论:
- 第一次 (-) - 兰诺丁丁B 的总合成证明了可行和有效的途径.
- 开发的方法展示了选择性还原性氨化和乙烯酸凝结的力量.
- 这种合成为进一步的生物研究提供了独特的天然产品.
相关概念视频
Protecting Groups for Aldehydes and Ketones: Introduction
Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
Protection of Alcohols
This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
Diazonium Group Substitution: –OH and –H
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.


