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CAREER: New Annulative Methods for the Synthesis of Complex Meroterpenes

职业生涯：合成复杂间萜的新环形方法

基本信息

批准号：
1554544
负责人：
Thomas Maimone
金额：
$ 60.55万
依托单位：
University of California-Berkeley
依托单位国家：
美国
项目类别：
Continuing Grant
财政年份：
2016
资助国家：
美国
起止时间：
2016-05-01 至 2021-04-30
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1554544&HistoricalAwards=false
关键词：
CAREER New Annulative Methods Synthesis

项目摘要

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.

有了这个职业奖，化学系的化学合成计划支持加州大学伯克利分校的托马斯·梅蒙教授的研究。 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。一种工具允许新的环被添加到分子结构中，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来开发一种称为多环聚异戊二烯化酰基间苯三酚的天然产物家族中分子结构的快速有效合成。这个家族的成员是保护神经元，并有潜在的用于治疗神经退行性疾病，如阿尔茨海默氏病。这一工作可望在有机合成和药物化学领域有广泛的应用。作为他的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。一个动手的研究组成部分已被设计为密集的夏季研究的指导下，加州大学伯克利分校的化学研究生。除了在社区学院一级的活动，这个职业奖还支持在小学一级的研究活动，作为在伯克利和奥克兰统一学区的湾区科学家在学校（BASIS）计划的一部分。这两项努力预计将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团体代表更大的湾区社区。Maimone教授正在开发新的合成反应，以促进复杂的多环化合物的建设。简单的化学原料双乙烯酮正在开发作为一种新型的成环试剂。此外，本研究还描述了高价碘络合物促进氧化碳-碳键重排的研究。这两个步骤共同作用产生多环聚异戊二烯化酰基间苯三酚的保守双环[3.3.1]壬烷三酮基序。该家族的成员显示出多种生物活性，包括抑制神经递质再摄取（贯叶金丝桃素）和增强胆碱乙酰转移酶（garsubellin A）。新的合成方法和获得这类天然产物的途径可能在有机合成和药物化学领域有应用。该教育计划包括编写关于杂环化合物合成的新教材，其对象是化学专业的高年级本科生和研究生。许多化学家在制药行业工作，其中杂环化学的知识很重要。