立体控制合成8-Hydroxycurvularol,一个带有修改的三甲烯骨架的塞斯基烯
Johanna M Masterson1, Erik J Sorensen1
1Department of Chemistry, Princeton University, Princeton, New Jersey 08544, United States.
研究人员合成了天然产品曲醇和8β-基曲醇,这两种基都具有潜在的抗癌活性. 开发了一种11个步骤的立体控制合成,克服了与四级立体中心相关的挑战.
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:
- 曲武醇和8β-氧曲武醇是由真菌衍生的三甲基.
- 这些化合物具有独特的分子结构,并具有作为抗癌剂的潜力.
研究的目的:
- 为了实现对curvularol (3) 和8β-hydroxycurvularol (4) 的立体控制合成.
- 开发一个简洁的策略来构建曲拉罗尔类型的分子框架.
主要方法:
- 从一个替代的环色开始进行了11步的合成.
- 关键步骤包括分子内达尔森斯甘酸凝结,立体选择性乳propargylation/OH silylation,以及一个5-exo dig 基循环.
- 氧化物14被用作一个前体.
主要成果:
- 已经成功合成了曲醇 (3) 和8β-基曲醇 (4).
- 通过介导的二氧化物14的降解产生了4.
- 为了合成3,需要对14进行激进的除氧化-脱氧化.
结论:
- 为曲拉罗尔类化合物制定了一种新而简洁的合成策略.
- 合成突出了在构建复杂的分子架构时特定的基和凝结反应的实用性.
- 开发的方法提供了潜在的抗癌三甲烯天然产品.
更多相关视频
07:59A Customizable Approach for the Enzymatic Production and Purification of Diterpenoid Natural Products
Published on: October 4, 2019
09:35Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
相关概念视频
Stereoisomerism of Cyclic Compounds
Stereoisomers
Stereoisomerism
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)