CAREER: New Advances in Five-Membered Ring Formation for Complex Molecule Synthesis

本项目致力于开发新的合成方法来形成五元环，最终合成了两个含有天然产物的五元环：脂氧合酶抑制剂tetrapetalone A和抗生素二萜guanacasteene A，它们已显示出对万古霉素耐药葡萄球菌的活性。除了在天然产物合成中的应用之外，这些新的转化可能提供对反应性的见解，例如烯丙基菌株和嵌合效应在加速周环过程中的重要性。例如，对天然产物四apetalone A的应用研究揭示了取代基在二烯基芳基酮Nazarov反应中的加速作用。此外，吡喃和α -酰基环戊烯酮之间的独特联系可能在复杂分子合成中得到广泛应用。PI将积极参与作为有兴趣从事科学事业的少数民族和妇女的导师和促进者。他将在加州大学伯克利分校的UC LEADS项目中担任三名少数族裔本科生的赞助人，在杰克逊州立大学担任少数族裔MAP项目的导师，并在奥克兰高中和奥克兰北极光中学担任化学推广项目的促进者。这些项目中的每一个都为大量少数民族和经济困难的学生提供服务。在有机和大分子化学项目的CAREER奖的支持下，加州大学伯克利分校化学系的Richmond Sarpong教授正在开发适用于复杂有机分子受控和高效合成的新反应。五元环存在于多种具有重要生物活性的天然产物中。虽然已经为五元环的合成开发了许多策略，但仍然需要进行合成转化，为这些类型的化合物提供必要的“手柄”，以转化为更复杂的产物。Sarpong教授还积极参与了各种旨在培养不同科学家群体的项目，每个项目都专门针对大量少数民族和经济困难的学生。他将在加州大学伯克利分校的UC LEADS项目中担任三名少数族裔本科生的赞助人，在杰克逊州立大学担任少数族裔MAP项目的导师，并在奥克兰高中和奥克兰北极光中学担任化学推广项目的促进者。

This project addresses the development of new synthetic methodology for the formation of five-membered rings, culminating in the synthesis of two five-membered ring containing natural products: the lipoxygenase inhibitor tetrapetalone A and the antibiotic diterpenoid guanacastepene A, which has shown activity against vancomycin resistant staphylococci. In addition to applications in natural product synthesis, these new transformations may offer insight into reactivity such as the importance of allylic strain and anchimeric effects in accelerating pericyclic processes. For example, investigations of applications to the natural product tetrapetalone A have revealed a substituent accelerating effect in a dienyl aryl ketone Nazarov reaction. Additionally, a unique connection has been made between pyrans and alpha-acyloxy cyclopentenones that may find broad application in complex molecule synthesis. The PI will be actively involved in serving as a mentor and facilitator for minority and women interested in pursuing careers in the sciences. He will serve as a sponsor for three minority undergraduates in the UC LEADS program at UC Berkeley, as a mentor for the minority MAP program at Jackson State University, and as a facilitator with chemistry outreach programs at Oakland High School and Northern Light Middle School in Oakland. Each of these programs serves a large number of minority and financially disadvantaged students.With the support of this CAREER award from the Organic and Macromolecular Chemistry Program, Professor Richmond Sarpong, of the Department of Chemistry at the University of California at Berkeley, is developing new reactions applicable to the controlled and efficient synthesis of complex organic molecules. Five-membered rings occur in a wide variety of natural products that possess important biological activity. Although a number of strategies have been developed for the synthesis of five-membered rings, there remains a need for synthetic transformations that provide these types of compounds with the necessary "handles" for conversion into more complex products. Professor Sarpong is also actively involved in a variety of programs designed to train a diverse group of scientists, with each of these programs specifically targeting a large number of minority and financially disadvantaged students. He will serve as a sponsor for three minority undergraduates in the UC LEADS program at UC Berkeley, as a mentor for the minority MAP program at Jackson State University, and as a facilitator with chemistry outreach programs at Oakland High School and Northern Light Middle School in Oakland.