Proline Sulfonamides Organocatalysis: Reaction Development and Application

在这个由化学部门化学合成项目资助的项目中，俄勒冈州立大学的Rich Carter教授正在开发脯氨酸磺酰胺催化合成立体化学丰富的构建模块的方法，并将其应用于天然产物的合成。脯氨酸磺酰胺基催化剂使化学家能够避免使用有毒金属来获取重要的化学构建块。联合首席研究员Paul Ha-Yeon Cheong正在通过计算探索这些反应的机制基础。通过该奖项合成的天然产物扩大了科学界可用的化学策略，并提高了萜烯结构的效率。这项研究的一个影响包括成立一家公司，部分基于这项工作，这为学生培训提供了机会。本研究通过有机合成与计算相结合的高度协作研究项目，为学生提供了独特的训练环境。本项目的重点是开发新的有机催化反应途径来获得二取代环己酮。立体中心在天然产物中的广泛存在使其构造成为有机化学研究的焦点；然而，仍然迫切需要实用的方法。这种化学的发展特点是计算和实验之间的密切关系，减少了反应时间的发展。本提案中开发和研究的方法将用于合成天然产物obtusanal A和wortmannin。

In this project funded by the Chemical Synthesis program of the Chemistry Division, Professor Rich Carter of Oregon State University is developing proline sulfonamide-catalyzed methods for the synthesis of stereochemically rich building blocks and applying these in natural product synthesis. Proline sulfonamide-based catalysts enable chemists to avoid the use of toxic metals to access important chemical building blocks. Co-principal investigator Paul Ha-Yeon Cheong is exploring the mechanistic underpinnings of these reactions computationally. Natural products being synthesized through this award expand the chemical strategies available to the scientific community and lead to efficiency gains in the construction of terpenes. An impact of this research includes the founding of a company, based in part on this work, which provides opportunities for student training. The research provides a unique training environment for students through a highly collaborative research program that integrates organic synthesis and computations.This project focuses on the development of novel organocatalytic reaction pathways to access disubstituted cyclohexenones. The widespread presence of stereogenic quaternary centers in natural products has made their construction a central focus of organic chemistry; however, practical methods continue to be critically needed. The development of this chemistry features a close relationship between computation and experiment that reduces reaction time development. Methodologies developed and studied in this proposal will be utilized in synthesizing the natural products obtusanal A and wortmannin.