催化酶选择性,保护 (+) - 二克罗安的无组总合成
Ryan M McFadden1, Brian M Stoltz
1Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Journal of the American Chemical Society
|June 15, 2006
概括
本研究提出了第一个对 (+) - 二克罗安的全合成,证实了它的自然配置. 这种高效,保护无组的方法利用了新的合成策略来合成天然产品.
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
背景情况:
- 迪克罗安是一种具有复杂结构的天然产品.
- 确定自然产品的绝对配置对于理解它们的生物活性至关重要.
研究的目的:
- 为了实现 (+) - 二克罗安的第一个enantioselective总合成.
- 为了确认天然产品的绝对配置.
- 开发一个高效和保护无组合成路径.
主要方法:
- 具有抗选择性的Tsuji合.
- 库马达 - - 芳香化战略
- 醇转化为氧-p-基的转换过程
主要成果:
- 在11个步骤中成功进行了 (+) - 二克罗安的全合成.
- 在天然产品合成中首次应用了对抗选择性Tsuji合.
- 展示了一种新的Kumada-aromatization和转化为的方法.
结论:
- 开发的合成路由是高效的,并保护无组的.
- (+) - 迪克罗安的绝对配置已经得到证实.
- 该研究展示了适用于天然产品合成的新型合成方法.
更多相关视频
相关概念视频
Enzymes
Inside living organisms, enzymes act as catalysts for many biochemical reactions involved in cellular metabolism. The role of enzymes is to reduce the activation energies of biochemical reactions by forming complexes with its substrates. The lowering of activation energies favor an increase in the rates of biochemical reactions.
Enzyme deficiencies can often translate into life-threatening diseases. For example, a genetic abnormality resulting in the deficiency of the enzyme G6PD...
Enzyme deficiencies can often translate into life-threatening diseases. For example, a genetic abnormality resulting in the deficiency of the enzyme G6PD...
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...
Catalytically Perfect Enzymes
The theory of catalytically perfect enzymes was first proposed by W.J. Albery and J. R. Knowles in 1976. These enzymes catalyze biochemical reactions at high-speed. Their catalytic efficiency values range from 108-109 M-1s-1. These enzymes are also called 'diffusion-controlled' as the only rate-limiting step in the catalysis is that of the substrate diffusion into the active site. Examples include triose phosphate isomerase, fumarase, and superoxide dismutase.
Introduction to Mechanisms of Enzyme Catalysis
For many years, scientists thought that enzyme-substrate binding took place in a simple "lock-and-key" fashion. This model stated that the enzyme and substrate fit together perfectly in one instantaneous step. However, current research supports a more refined view scientists call induced fit. The induced-fit model expands upon the lock-and-key model by describing a more dynamic interaction between enzyme and substrate. As the enzyme and substrate come together, their interaction causes a mild...
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...
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.


