Advancing Synthetic Methodology through Total Synthesis of Complex Molecules

美国加州大学圣巴巴拉分校的Armen Zakarian教授在美国国家科学基金会化学分部化学合成项目资助下，正在开发新的方法和合成策略，以制备一系列具有有用性能的有机材料。这些方法旨在缩短从现成资源合成这些材料的时间，因此更经济、更节能、更少浪费。使用新的化学工具可以制备的化合物类型主要应用于药物研究和工业，其次应用于材料和农业科学。这个研究项目的目标是双重的。第一个主要目标是发展现代碳氢功能化方法，用于合成苯并呋喃和含苯并呋喃的生物医学天然产物，如加兰他明。铜催化的芳基C-H直接功能化方法为在温和条件下获得功能化苯并呋喃提供了一条很有前途的途径。目前正在研究其范围及其在加兰他敏简明合成中的应用。第二个目标是发展镧系元素催化Diels Alder反应中二烯的活化。这种方法的特点是全合成muironolide A，这是一种非常罕见的海洋天然产物，具有前景但尚未开发的生物医学潜力。在扎卡里安小组的研究生和参与加州大学圣巴巴拉分校SciTrak项目的地区小学生和教师之间，正在制定一项外展计划。

ABSTRACTIn this project funded by the Chemical Synthesis program of the Chemistry Division of the National Science Foundation, Professor Armen Zakarian of the University of California, Santa Barbara, is developing new methods and synthetic strategies for the preparation of a broad range of organic materials with useful properties. These methods are designed to make the synthesis of such materials from readily available sources shorter, and therefore more economical, energy-efficient, and less wasteful. The types of compounds that can be prepared using the new chemical tools find application primarily in pharmaceutical research and industry, and secondarily in materials and agricultural sciences.The goals of this research project are two-fold. The first major goal is the development of modern C-H functionalization methods for the synthesis of benzofurans and benzofuran-containing natural products of biomedical significance, such as galanthamine. A copper-catalyzed direct aryl C-H functionalization method has been identified as highly promising to provide a path to functionalized benzofurans under mild conditions. Studies of its scope and application in the concise synthesis of galanthamine are being currently pursued. The second goal is the development of lanthanide catalysis for activation of dienes in the Diels Alder reaction. This approach features in the total synthesis of muironolide A, an exceedingly rare marine natural product with promising but unexplored biomedical potential. An outreach program is being developed between graduate students in the Zakarian group and area elementary school students and teachers involved in the SciTrak program hosted at UC Santa Barbara.