CAREER: New Annulative Methods for the Synthesis of Complex Meroterpenes

通过这个职业奖，化学系的化学合成项目支持加州大学伯克利分校的Thomas Maimone教授的研究。Maimone教授正在开发新的有机合成工具，旨在促进复杂多环化合物的构建。一种工具允许在分子结构中添加新的环，另一种工具允许通过氧化反应改变环的大小。Maimone教授正在应用这些合成工具，开发一种称为聚环聚丙烯酰化酰基间苯三醇的天然产物家族的分子结构的快速有效的合成。该家族的成员具有保护神经元的作用，对治疗阿尔茨海默病等神经退行性疾病有潜在的用途。这项工作在有机合成和药物化学领域具有广泛的应用前景。作为他项目的教育组成部分，Maimone教授正在开发一个研究研讨会，重点是向社区大学生介绍合成有机化学研究。在加州大学伯克利分校化学研究生的指导下，设计了一个动手研究部分，用于密集的夏季研究。除了社区大学层面的活动，该职业奖还支持小学层面的研究活动，作为伯克利和奥克兰联合学区湾区学校科学家（BASIS）计划的一部分。这两项努力都有望增加对科学领域的兴趣，特别是化学，在一个高度多样化的学生群体中，代表着更大的湾区社区。迈莫尼教授正在开发新的合成反应，以促进复杂多环化合物的构建。作为一种新型环化试剂，简单原料化学二烯正在被开发。此外，本研究描述了高价碘配合物促进氧化碳-碳键重排的研究。这两个步骤共同作用产生了保守的双环[3.3.1]壬烷三酮基序的多环聚丙烯酰化酰基间苯三酚。该家族的成员表现出多种生物活性，包括抑制神经递质再摄取（hyperperforin）和增强胆碱乙酰转移酶（garsubellin a）。这些新的合成方法和该类天然产物的获得在有机合成和药物化学等领域具有广泛的应用前景。该教育计划包括开发新的杂环合成课程材料，其目标是高级本科化学专业和研究生。许多化学家在制药行业工作，在那里杂环化学的知识是很重要的。

With this CAREER Award, the Chemical Synthesis Program of the Division of Chemistry is supporting the research of Professor Thomas Maimone of the University of California, Berkeley. Professor Maimone is developing new tools for organic synthesis that are designed to facilitate the construction of complex polycyclic compounds. One tool allows new rings to be added to a molecular structure, and another allows the size of the ring to be changed by an oxidation reaction. Professor Maimone is applying these synthetic tools to develop rapid and efficient syntheses of molecular structures in a family of natural product called polycyclic polyprenylated acylphloroglucinols. Members of this family of are protect neurons and have potential use for the treatment of neurodegenerative conditions such as Alzheimer's disease. This work is expected to have broad applications in the field of organic synthesis as well as medicinal chemistry. As the educational component of his project, Professor Maimone is developing a research symposium that focuses on introducing community college students to synthetic organic chemistry research. A hands-on research component has been designed for intensive summer research under the mentorship of a UC-Berkeley graduate chemistry student. In addition to activities at the community college level, this CAREER Award also supports research activities at the elementary school level as part of the Bay Area Scientists in Schools(BASIS) program in the Berkeley and Oakland unified school districts. Both of these endeavors are expected to increase interest in science fields, particularly chemistry, across a highly diverse student body representative of the larger Bay Area community.Professor Maimone is developing new synthetic reactions to facilitate the construction of complex polycyclic compounds. The simple feedstock chemical diketene is being developed as a novel annulation reagent. In addition, this research describes the study of oxidative carbon-carbon bond rearrangements promoted by hypervalent iodine complexes. These two steps work together to produce the conserved bicyclo [3.3.1] nonane trione motif of the polycyclic polyprenylated acylphloroglucinols. Members of this family show a variety of biological activities, including inhibition of neurotransmitter reuptake (hyperforin) and choline acetyltransferase enhancement (garsubellin A). The new synthetic methods and access to this family of natural products may have applications in the fields of organic synthesis and medicinal chemistry. The educational plan includes the development of new course material on the synthesis of heterocycles, which is targeted towards advanced undergraduate chemistry majors and graduate students. Many chemists work in the pharmaceutical industry where such knowledge of heterocyclic chemistry is important.