Natural Product Inspired Synthetic Methods

天然产物启发的合成方法

• 批准号: RGPIN-2014-04891
• 负责人: Pagenkopf, Brian
• 金额: $ 2.48万
• 依托单位: University of Western Ontario
• 依托单位国家: 加拿大
• 项目类别: Discovery Grants Program - Individual
• 财政年份: 2015
• 资助国家: 加拿大
• 起止时间: 2015-01-01 至 2016-12-31
• 项目状态: 已结题
• 来源: https://www.nserc-crsng.gc.ca/ase-oro/Details-Detailles_eng.asp?id=588083
• 关键词: Natural; Product; Inspired; Synthetic; Methods

The Pagenkopf group has been engaged in four primary areas of research within organic synthesis. We plan to continue the discovery of new reactions of donor-acceptor cyclopropanes and exploring applications in natural product synthesis. A key natural product we plan to prepare is the anti-cancer compound streptorubin B, and the approach features a new strategy that utilizes a cyclopropane incorporated into a macrocycle to assemble one of the pyrroles. The successful outcome could be broadly applicable to the synthesis of analogs and other members of the prodigiosin family. Secondly, the group has been engaged in the development of new catalysts for the synthesis of tetrahydrofurans (THF’s) from hydroxy olefins under green conditions by utilizing air as the stoichiometric oxidant. Some key synthetic targets under investigation include the biologically active natural products amphidinolide C and biselide A, both of which show impressive anti-cancer activity. And third, we have been engaged in the synthesis of novel siloles and exploration of their properties. Through structural modification by chemical synthesis new materials with useful functional properties are being developed. And forth, we have recently begun exploring the reactions of a new class of donor-acceptor cyclobutanes, and plans to discover new reactions are described. The importance of synthetic chemistry to materials science and the pharmaceutical industry is well understood as synthetic chemistry is a fundamental aspect of these industries, which are important contributors to the Canadian economy. New, useful synthetic methods are required to expand the tool-box of chemical reactions available to the synthetic, medicinal or process chemist. In this proposal, plans have been put forth to develop new chemical transformations which will assist the chemical community in their synthetic endeavors. In addition, an extended knowledge of chemical reactivity will be gained through natural product synthesis. These efforts provide excellent training for careers in the pharmaceutical and related industries. The silole based materials being explored have the potential to directly impact biomedical and environmental chemistry by, for example, aiding in the early detection of disease through improving sensitivity over some existing methods.

Pagenkopf组在有机合成中参与了四个主要研究领域。我们计划继续发现捐助者环丙烷的新反应，并探索自然产品合成中的应用。我们计划准备的一个关键天然产品是抗癌化合物链球菌B，该方法采用了一种新策略，该策略利用掺入大环的环丙烷来组装其中一种吡咯。成功的结果可能广泛地适用于类似物和Prodigiosin家族的其他成员的综合。其次，该小组一直从事新的催化剂，用于在绿色条件下利用空气作为浓氧化物，从羟基烯烃合成四氢呋喃（THF）。所研究的一些关键合成靶标包括生物活性的天然产物两栖类药物C和双替尼A，两者均表现出令人印象深刻的抗癌活性。第三，我们一直参与合成新型硅和对其性质的探索。通过化学合成的结构修饰，正在开发具有有用功能特性的新材料。以及我们最近开始探索一类新的捐赠者环形车生物的反应，并描述了发现新反应的计划。 合成化学对材料科学和制药行业的重要性被充分理解为合成化学是这些行业的一个基本方面，这是加拿大经济的重要贡献。需要新的，有用的合成方法来扩展合成，药用或过程化学家可用的化学反应工具箱。在此提案中，已经制定了计划开发新的化学转化，这将有助于化学界的合成努力。此外，将通过自然产物合成获得扩展的化学反应性知识。这些努力为制药和相关行业的职业提供了出色的培训。 探索基于硅洛的材料有可能通过改善对某些现有方法的敏感性来帮助早期发现疾病的生物医学和环境化学。