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

该项目致力于开发用于形成五元环的新合成方法，最终合成两种含五元环的天然产物：脂氧合酶抑制剂tetrapetalone A和抗生素二萜类化合物guanacastepene A，其对万古霉素耐药葡萄球菌具有活性。除了在天然产物合成中的应用外，这些新的转化可能会提供对反应性的深入了解，例如在加速周环过程中烯丙基应变和邻位效应的重要性。例如，对天然产物四瓣花酮A的应用的研究已经揭示了在二烯基芳基酮Nazarov反应中的取代基加速效应。此外，在吡喃和α-酰氧基环戊烯酮之间已经建立了独特的联系，这可能在复杂分子合成中找到广泛的应用。PI将积极参与担任有兴趣从事科学事业的少数民族和妇女的导师和促进者。他将担任三个少数民族本科生在加州大学伯克利分校领导计划的赞助商，作为少数民族地图计划在杰克逊州立大学的导师，并作为一个在奥克兰高中和北方轻中学化学推广计划的促进者。在有机与高分子化学项目的支持下，加州大学伯克利分校化学系的里士满·萨蓬教授正在开发适用于复杂有机分子的可控和有效合成的新反应。五元环存在于各种具有重要生物活性的天然产物中。虽然已经开发了许多策略用于合成五元环，但仍然需要合成转化，其为这些类型的化合物提供必要的“把手”以转化为更复杂的产物。Sarpong教授还积极参与各种旨在培养多元化科学家群体的计划，这些计划中的每一个都专门针对大量少数民族和经济困难的学生。他将担任三个少数民族本科生在加州大学伯克利分校领导计划的赞助商，作为少数民族地图计划在杰克逊州立大学的导师，并作为一个在奥克兰高中和北方轻中学化学推广计划的促进者。

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.