乙甲和乙甲的总合成
K C Nicolaou1, Hanfeng Ding, Jean-Alexandre Richard
1Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering Sciences, Agency for Science, Technology and Research, 11 Biopolis Way, The Helios Block, #03-08, Singapore 138667. kcn@scripps.edu
Journal of the American Chemical Society
|February 27, 2010
概括
研究人员合成了echinolines A和B,这些天然化合物具有独特的碳框架. 这项研究详细介绍了它们的总合成,使用了新的催化环和二氧化介导的环闭方法.
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:
- 乙基诺A和B是天然存在的化合物,具有独特的[3.5.5.7]碳框架.
- 这些天然产品的结构复杂性构成了重要的合成挑战.
研究的目的:
- 为了实现埃基诺林A和B的总合成,在酶体和酶体两种形式.
- 探索新的合成方法来构建复杂的自然产品.
主要方法:
- 开发一种新的分子内催化循环化反应.
- 采用三二氧化介导的环闭,以形成关键键键.
- 立体选择性合成的两个反体和种族混合物.
主要成果:
- 已经成功地完成了乙素A和B的总合成.
- 合成路径确定了新型环和环闭反应的可行性.
- 得到了目标化合物的体和体形式.
结论:
- 开发的合成策略提供了一个有效的途径,以echinolines A和B.
- 这项研究强调了催化循环和二介导反应在复杂分子合成中的实用性.
- 这项工作为自然产品合成和方法开发的更广泛领域做出了贡献.
相关概念视频
Chirality in Nature
Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid. The...
Prochirality
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
Production of Pharmaceuticals
Industrial insulin production uses genetically engineered E. coli expressing a proinsulin gene controlled by a tryptophan promoter and containing a methionine linker for later cleavage. The cells also carry ampicillin resistance for selective growth. Seed cultures are stored at −80 °C and production begins by thawing a small amount to inoculate starter cultures, which are progressively scaled to a 50,000-L bioreactor. In the bioreactor, E. coli grow in nutrient-rich media under sterile, tightly...
Direct-Acting Cholinergic Agonists: Pharmacokinetics
Direct-acting cholinergic agonists, such as synthetic choline esters and naturally occurring alkaloids, exert their effects by enhancing the actions of acetylcholine and stimulating the parasympathetic nervous system. Synthetic choline esters share structural similarities with acetylcholine. For example, they have a positively charged quaternary ammonium or onium group, contributing to their hydrophilic characteristics. As a result, they are poorly absorbed in the body through oral...
Sharpless Epoxidation
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...


