Strategy Driven Synthesis of Complex Alkaloids

在化学系化学合成计划的支持下，加州大学伯克利分校的托马斯·迈蒙教授将研究构建复杂的含氮分子的新合成策略。这项工作的核心是识别能够导致产生具有高整体效率的拓扑独特的靶分子的强有力的简化转化。为该计划选择的目标挑战了当前复杂分子合成的最先进水平。这些努力的结果预计将对具有社会重要性的有机化学合成领域产生积极影响，该领域用于生产药品、农用化学品和工业材料。这项工作也将对将来成为这些领域的科学家的研究生进行智力激励培训。此外，这笔赠款使湾区小学生以及当地社区大学转学学生能够广泛开展以科学为重点的外展活动。Maimone教授正在研究具有重要生物学特性和不同寻常的分子结构的菊双胺和桃金娘内酯家族成员的复杂生物碱合成。这些生物合成的神秘分子多年来一直被证明是有机化学合成的具有挑战性的目标。Maimone教授的工作将产生构建具有挑战性的C-C键键和卤化SP3立体中心的新策略，并将提出使用小环状试剂形成环的新方法。这项工作不仅将促进合成科学的发展，而且还将为进一步的科学研究创造大量稀有的天然产物。作为该项目的一部分，Maimone教授也在培训他的同事，为他们在化学工业和学术界的职业生涯做好准备。这一奖项反映了NSF的法定使命，并通过使用基金会的智力优势和更广泛的影响审查标准进行评估，被认为值得支持。

With the support of the Chemical Synthesis program in the Division of Chemistry, Professor Thomas Maimone of the University of California, Berkeley will study new synthetic strategies for the construction of complex, nitrogen-containing molecules. At the core of this work is the identification of powerfully simplifying transformations that can lead to the production of topologically unique target molecules with high overall efficiency. The targets chosen for this program challenge the current state-of-the-art in complex molecule synthesis. Results of these endeavors are expected to have a positive impact across the societally important field of organic chemical synthesis which is used to produce medicines, agrochemicals, and materials industrially. This work will also serve as intellectually stimulating training for graduate students who will become future scientists in these fields. Moreover, this grant enables wide-reaching science-focused outreach for Bay Area elementary school students as well as local community college transfer students. Professor Maimone is studying complex alkaloid syntheses of members of the caulamidine and myrmicarin families which have important biological properties and unusual molecular architectures. These biosynthetically mysterious molecules have proven challenging as targets for organic chemical synthesis for many years. Professor Maimone’s work will generate new strategies to construct challenging C–C bond linkages and halogenated Sp3 stereocenters and will also put forth new methods for ring formation using small annulation reagents. This work will not only advance the science of synthesis but allow for the construction of ample quantities of rare natural products for further scientific study. As a part of this project, Professor Maimone is also training his coworkers and preparing them for careers in chemical industries and academia.This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.