Diastereoselective Formation of Cyclopentanes and Gamma-Lactones Mediated by Manganese(III)
锰(III)介导的环戊烷和γ-内酯的非对映选择性形成
基本信息
- 批准号:EP/C006054/2
- 负责人:
- 金额:--
- 依托单位:
- 依托单位国家:英国
- 项目类别:Research Grant
- 财政年份:2007
- 资助国家:英国
- 起止时间:2007 至 无数据
- 项目状态:已结题
- 来源:
- 关键词:
项目摘要
The rapid and selective synthesis of biologically important molecules (e.g. pharmaceuticals) is an important and continuing goal for chemists. It is necessary to be able to make such molecules using efficient processes which, as far as possible, are environmentally benign. This proposal involves the development of an exceedingly mild method for the selective construction of a certain class of biologically relevant compounds (namely poly-substituted chiral cyclopentanes and gamma-lactones). There are many methods available for the synthesis of chiral cyclopentanes however the method to be developed within this proposal has the potential to be the most mild and straightforward method for the construction of such systems. Our preliminary results indicate that we can synthesise chiral cyclopentanes via a free radical process, simply by heating an appropriate compound in alcohol in the presence of manganese(III) acetate. This process is operationally straightforward to conduct and does not require any special experimental procedures. The formation of chiral cyclopentanes using free-radical chemistry has been previously reported. Most of these reports utilise organotin compounds to effect the desired transformation. Organotin compounds are highly toxic and present not only a disposal hazard but are often difficult to remove completely from the desired product. The use of manganese(III) acetate overcomes these issues; the manganese by-products are readily removed using standard techniques. Further important benefits of using manganese(III) acetate over organotin compounds include: the ability to produce more highly functionalised products which are therefore more readily transformed into the desired materials; the potential to use a wider variety of radical precursors which, not only adds flexibility to the synthesis, but also allows a wider variety of compounds to be synthesised. Both of these advantages will be fully explored in this research. Another process which may occur during manganese(III) acetate mediated reactions is the formation of heterocyclic rings (e.g. gamma-lactones). A further aim of this proposal is to develop a selective synthesis of gamma-lactones bearing up to four contiguous chiral centres using manganese(III) acetate chemistry. These molecules will contain one all carbon chiral centre (a quaternary centre). The selective synthesis of chiral molecules carrying quaternary centres remains a challenging area for synthetic organic chemists. Our aim is to develop a very mild method for the construction of such systems. We currently have an efficient route to a functionally-differentiated molecule bearing a quaternary centre which we believe has the potential to be a very valuable building block for organic chemists. The mild synthetic methods developed during the initial phases of this project will be demonstrated in the efficient syntheses of a variety of biologically and structurally interesting molecules. In summary, the aim of this proposal is to develop an exceptionally mild and operational simple method for the highly selective synthesis of cyclopentanes and gamma-lactones which will be applicable to a wide range of biologically and structurally interesting molecules.
快速、选择性地合成生物学上重要的分子(例如药物)是化学家的一个重要且持续的目标。有必要能够使用尽可能对环境无害的高效工艺来制造此类分子。该提案涉及开发一种极其温和的方法,用于选择性构建某一类生物学相关化合物(即多取代手性环戊烷和γ-内酯)。有许多方法可用于合成手性环戊烷,但本提案中开发的方法有可能成为构建此类系统的最温和、最直接的方法。我们的初步结果表明,我们可以通过自由基过程合成手性环戊烷,只需在乙酸锰(III)存在下加热酒精中的适当化合物即可。该过程操作简单,不需要任何特殊的实验程序。先前已报道过使用自由基化学形成手性环戊烷。这些报告中的大多数利用有机锡化合物来实现所需的转化。有机锡化合物具有剧毒,不仅存在处置危险,而且通常难以从所需产品中完全去除。醋酸锰(III)的使用克服了这些问题;使用标准技术很容易去除锰副产物。与有机锡化合物相比,使用乙酸锰 (III) 的其他重要优势包括:能够生产更高功能化的产品,因此更容易转化为所需的材料;使用更广泛的自由基前体的潜力,这不仅增加了合成的灵活性,而且还允许合成更广泛的化合物。本研究将充分发挥这两个优点。乙酸锰(III)介导的反应期间可能发生的另一个过程是杂环(例如γ-内酯)的形成。该提案的另一个目标是使用乙酸锰(III)化学来开发具有多达四个连续手性中心的γ-内酯的选择性合成。这些分子将包含一个全碳手性中心(四元中心)。带有四级中心的手性分子的选择性合成对于合成有机化学家来说仍然是一个具有挑战性的领域。我们的目标是开发一种非常温和的方法来构建此类系统。我们目前有一条有效的途径来获得具有四级中心的功能分化分子,我们相信这种分子有可能成为有机化学家非常有价值的构建模块。在该项目的初始阶段开发的温和合成方法将在各种生物学和结构上有趣的分子的有效合成中得到证明。总之,该提案的目的是开发一种极其温和且操作简单的方法,用于高选择性合成环戊烷和γ-内酯,该方法将适用于广泛的生物学和结构上有趣的分子。
项目成果
期刊论文数量(0)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)
数据更新时间:{{ journalArticles.updateTime }}
{{
item.title }}
{{ item.translation_title }}
- DOI:
{{ item.doi }} - 发表时间:
{{ item.publish_year }} - 期刊:
- 影响因子:{{ item.factor }}
- 作者:
{{ item.authors }} - 通讯作者:
{{ item.author }}
数据更新时间:{{ journalArticles.updateTime }}
{{ item.title }}
- 作者:
{{ item.author }}
数据更新时间:{{ monograph.updateTime }}
{{ item.title }}
- 作者:
{{ item.author }}
数据更新时间:{{ sciAawards.updateTime }}
{{ item.title }}
- 作者:
{{ item.author }}
数据更新时间:{{ conferencePapers.updateTime }}
{{ item.title }}
- 作者:
{{ item.author }}
数据更新时间:{{ patent.updateTime }}
Jonathan Burton其他文献
Expanding the Role of the Pharmacist
扩大药剂师的作用
- DOI:
- 发表时间:
2018 - 期刊:
- 影响因子:0
- 作者:
N. Gray;Jonathan Burton;Roisin Campbell;J. McDonagh - 通讯作者:
J. McDonagh
The Effects of Personalized Feedback on Participation and Reporting in Mobile App Data Collection
个性化反馈对移动应用程序数据收集中参与和报告的影响
- DOI:
- 发表时间:
2020 - 期刊:
- 影响因子:4.1
- 作者:
Alexander Wenz;A. Jäckle;Jonathan Burton;M. Couper - 通讯作者:
M. Couper
The Idiosyncratic Impact of an Aggregate Shock: The Distributional Consequences of COVID-19
总体冲击的特殊影响:COVID-19 的分配后果
- DOI:
- 发表时间:
2020 - 期刊:
- 影响因子:0
- 作者:
Brendan Read;Hamish Low;A. Jäckle;Paul Fisher;Thomas F. Crossley;Jonathan Burton;M. Benzeval - 通讯作者:
M. Benzeval
A review of methodological research pertinent to longitudinal survey design and data collection
与纵向调查设计和数据收集相关的方法研究综述
- DOI:
- 发表时间:
2005 - 期刊:
- 影响因子:0
- 作者:
Peter Lynn;N. Buck;Jonathan Burton;Jäckle Annette;Heather Laurie - 通讯作者:
Heather Laurie
Understanding Society Innovation Panel Wave 5: Results from Methodological Experiments
了解社会创新小组第五波:方法实验的结果
- DOI:
- 发表时间:
2013 - 期刊:
- 影响因子:0
- 作者:
Jonathan Burton;Katrin Auspurg;C. Cullinane;Laura Fumagelli;Maria Iacovou;A. Jäckle;Olena Kaminska;Peter Lynn;Paul Mathews;G. Nicolaas;C. Nicoletti;Cong Ye;Basit Zafar - 通讯作者:
Basit Zafar
Jonathan Burton的其他文献
{{
item.title }}
{{ item.translation_title }}
- DOI:
{{ item.doi }} - 发表时间:
{{ item.publish_year }} - 期刊:
- 影响因子:{{ item.factor }}
- 作者:
{{ item.authors }} - 通讯作者:
{{ item.author }}
{{ truncateString('Jonathan Burton', 18)}}的其他基金
Total synthesis of biologically active lactone/lactam natural products
生物活性内酯/内酰胺天然产物的全合成
- 批准号:
EP/Y026888/1 - 财政年份:2023
- 资助金额:
-- - 项目类别:
Fellowship
UK-Australia Network Promoting Longitudinal Survey Methods and Analysis
英国-澳大利亚网络推广纵向调查方法和分析
- 批准号:
ES/J019216/1 - 财政年份:2012
- 资助金额:
-- - 项目类别:
Research Grant
Methodology for, and Synthesis of Biologically Active Pyrrolidinone Natural Products.
生物活性吡咯烷酮天然产物的方法学和合成。
- 批准号:
EP/J004499/1 - 财政年份:2012
- 资助金额:
-- - 项目类别:
Research Grant
Co-ordinator for the Survey Design and Measurement Initiative
调查设计和测量计划协调员
- 批准号:
RES-175-31-0001 - 财政年份:2008
- 资助金额:
-- - 项目类别:
Research Grant
相似国自然基金
基于泛化齐次化方法的奇异多智能体系统有限时间时变编队控制
- 批准号:62303365
- 批准年份:2023
- 资助金额:30 万元
- 项目类别:青年科学基金项目
非完全合作网络下多无人机分组编队包围控制
- 批准号:62373097
- 批准年份:2023
- 资助金额:50 万元
- 项目类别:面上项目
执行器饱和约束下网络化机器人系统的预定时间编队控制
- 批准号:62303430
- 批准年份:2023
- 资助金额:30 万元
- 项目类别:青年科学基金项目
集群-车辆-农田共融环境下机器人系统区域作业的协同感知与编队控制
- 批准号:52375107
- 批准年份:2023
- 资助金额:50 万元
- 项目类别:面上项目
基于深度强化学习的多无人船协同编队与路径规划
- 批准号:52371372
- 批准年份:2023
- 资助金额:50 万元
- 项目类别:面上项目
相似海外基金
Domino - Computational Fluid Dynamics Modelling of Ink Droplet Breakup for Mitigating Mist Formation during inkjet printing
Domino - 墨滴破碎的计算流体动力学模型,用于减轻喷墨打印过程中的雾气形成
- 批准号:
10090067 - 财政年份:2024
- 资助金额:
-- - 项目类别:
Collaborative R&D
Cosmic Renaissance: The Last Chance for Planet Formation Around Dying Stars
宇宙复兴:垂死恒星周围行星形成的最后机会
- 批准号:
DP240101150 - 财政年份:2024
- 资助金额:
-- - 项目类别:
Discovery Projects
Cell Wall Formation in Rod Shaped Bacteria
杆状细菌细胞壁的形成
- 批准号:
BB/Y003187/1 - 财政年份:2024
- 资助金额:
-- - 项目类别:
Research Grant
Dark Data from the White Continent: New Light on Five Decades of Vertebrate Paleontology Collections from the Triassic Fremouw Formation of Antarctica
来自白色大陆的暗数据:对南极洲三叠纪 Fremouw 组的五个十年的脊椎动物古生物学收藏的新认识
- 批准号:
2313242 - 财政年份:2024
- 资助金额:
-- - 项目类别:
Standard Grant
CAREER: Measurement of Photochemical Mechanisms, Rates, and Pathways of Radical Formation in Complex Organic Compounds
职业:测量复杂有机化合物中自由基形成的光化学机制、速率和途径
- 批准号:
2340926 - 财政年份:2024
- 资助金额:
-- - 项目类别:
Continuing Grant