Advancing Synthetic Methodology through Total Synthesis of Complex Molecules

摘要在这个由美国国家科学基金会化学部化学合成计划资助的项目中，加州大学圣巴巴拉分校的Armen Zakarian教授正在开发新的方法和合成策略，用于制备具有有用性质的广泛的有机材料。这些方法被设计成使得从容易获得的来源合成这些材料更短，并且因此更经济、节能和更少浪费。使用新的化学工具可以制备的化合物类型主要应用于制药研究和工业，其次是材料和农业科学。该研究项目的目标是双重的。第一个主要目标是发展现代C-H官能化方法，用于合成具有生物医学意义的苯并呋喃和含苯并呋喃的天然产物，如加兰他敏。铜催化的芳基C-H直接官能化方法已被确定为在温和条件下提供官能化苯并呋喃的路径的高度有前途的方法。目前正在对其范围和在加兰他敏简明合成中的应用进行研究。第二个目标是开发镧系元素催化剂用于活化Diels桤木反应中的二烯。这种方法的特点是全合成的muironeA，一个非常罕见的海洋天然产品，有前途的，但未开发的生物医学潜力。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个推广计划。

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.