Natural Product Inspired Synthetic Methods

Pagenkopf小组一直致力于有机合成领域的四个主要研究领域。我们计划继续发现给体-受体环丙烷的新反应，并探索其在天然产物合成中的应用。我们计划制备的一个关键天然产品是抗癌化合物链霉菌红素B，该方法的特点是采用了一种新的策略，将环丙烷结合到一个大环中来组装其中一个吡咯。这一成功的结果可能广泛适用于类似物和灵芝菌素家族的其他成员的合成。其次，该小组一直致力于开发利用空气作为化学计量比氧化剂，在绿色条件下由羟基烯烃合成四氢呋喃(THF)的新型催化剂。正在研究的一些关键合成目标包括具有生物活性的天然产物苯二内酯C和双内酯A，这两种化合物都具有令人印象深刻的抗癌活性。第三，我们一直致力于合成新型硅烷并探索它们的性质。通过化学合成进行结构修饰，正在开发出具有实用功能的新材料。第四，我们最近开始探索一类新的给体-受体环丁烷的反应，并描述了发现新反应的计划。合成化学对材料科学和制药工业的重要性是众所周知的，因为合成化学是这些行业的一个基本方面，这些行业是加拿大经济的重要贡献者。需要新的、有用的合成方法来扩大合成、医药或过程化学家可用的化学反应工具箱。在这项提案中，提出了开发新的化学转化的计划，这将有助于化学界的合成努力。此外，还将通过天然产物合成获得有关化学反应的扩展知识。这些努力为制药和相关行业的职业生涯提供了极好的培训。正在探索的基于竖井的材料具有直接影响生物医学和环境化学的潜力，例如，通过提高对一些现有方法的灵敏度来帮助疾病的早期检测。

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.