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

该项目致力于开发形成五元环的新合成方法，最终合成两个包含天然产物的五元环：脂氧合酶抑制剂四氢呋喃甲素A和抗生素二萜鸟苷A，后者已显示出抗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外，这些新的转化还可能提供对反应性的洞察，例如烯丙基应变和锚定效应在加速周环过程中的重要性。例如，对天然产物四氢呋喃A的应用研究揭示了取代基在二烯基芳基酮纳扎罗夫反应中的加速作用。此外，吡喃和α-酰氧基环戊酮之间有一种独特的联系，这可能会在复杂分子合成中找到广泛的应用。非政府组织将积极参与为少数群体和有兴趣从事科学事业的妇女提供指导和促进。他将担任加州大学伯克利分校UC Leads计划的三名少数族裔本科生的赞助商，杰克逊州立大学少数族裔地图计划的导师，以及奥克兰奥克兰高中和北极光中学化学推广计划的促进者。每个项目都服务于大量少数族裔和经济困难的学生。在有机化学和高分子化学项目这一职业奖项的支持下，加州大学伯克利分校化学系的里士满·萨邦教授正在开发适用于复杂有机分子可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。虽然已经开发了一些合成五元环的策略，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品。萨蓬教授还积极参与了各种旨在培训不同科学家群体的项目，每个项目都专门针对大量少数族裔和经济困难的学生。他将担任加州大学伯克利分校UC Leads计划的三名少数族裔本科生的赞助商，杰克逊州立大学少数族裔地图计划的导师，以及奥克兰奥克兰高中和北极光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.