Innovative Approaches to Macrocyclic Natural Products

大环天然产物的创新方法

基本信息

批准号：
1665246
负责人：
Rich Carter
金额：
$ 50万
依托单位：
Oregon State University
依托单位国家：
美国
项目类别：
Continuing Grant
财政年份：
2017
资助国家：
美国
起止时间：
2017-05-01 至 2020-04-30
项目状态：
已结题

来源：
https://www.nsf.gov/awardsearch/showAward?AWD_ID=1665246&HistoricalAwards=false
关键词：
Innovative Approaches Macrocyclic Natural Products

项目摘要

The Chemical Synthesis Program of the Chemistry Division supports this project by Professor Rich G. Carter. Professor Carter and his co-investigator, Professor Cheong, are both a faculty members in the Department of Chemistry at Oregon State University. His group is exploring the chemistry of an exciting new series of polyketide natural products called the mandelalides and madeirolides. The overarching goal of this proposal is to develop innovative methods for the construction of these natural products, which advance the field in both reaction and strategy development. These compounds have shown promising cytotoxic and antifungal activities. The project brings together expertise in both experimental (Professor Carter) and computational (Professor Cheung) organic chemistry. Professor Carter's group is well positioned to provide the highest level of education and training for students underrepresented in science. Professional development efforts for students participating in this project are integrated into the program. In addition, outreach activities to engage the broader community on the importance of chemistry are planned. The total synthesis of complex natural products has proven to be an important test bed for the development of new synthetic strategy as well as for the validation of novel chemical methodologies. The proposed syntheses of mandelalides A-B and madeirolide A push the limits of modern organic synthesis. One new methods is the development of a reliable asymmetric dihydroxylation of cis-alkenes to rapidly access trans diols, which is integral to these projects. In addition, the proposed syntheses showcase silver-catalyzed cyclizations of propargylic benzoates. The educational plan includes professional development training for graduate students through an NSF Graduate Research Trainingship Innovation in Graduate Education (NRT IGE) grant at Oregon State University and community engagement through outreach activities at one or two additional schools within the State of Oregon.

化学部化学合成项目支持Rich G. Carter教授的这一项目。卡特教授和他的合作研究员张教授都是俄勒冈州立大学化学系的教员。他的团队正在探索一系列令人兴奋的新聚酮化合物天然产物（称为扁桃内酯和马黛罗内酯）的化学成分。该提案的总体目标是开发构建这些天然产物的创新方法，从而推动该领域的反应和策略开发。这些化合物显示出有希望的细胞毒性和抗真菌活性。该项目汇集了实验（卡特教授）和计算（张教授）有机化学方面的专业知识。卡特教授的团队处于有利地位，可以为科学领域代表性不足的学生提供最高水平的教育和培训。参与该项目的学生的专业发展努力已纳入该计划。此外，还计划开展外展活动，让更广泛的社区了解化学的重要性。复杂天然产物的全合成已被证明是开发新合成策略以及验证新化学方法的重要试验台。所提出的扁桃内酯 A-B 和马黛罗内酯 A 的合成突破了现代有机合成的极限。一种新方法是开发可靠的顺式烯烃不对称二羟基化，以快速获得反式二醇，这是这些项目不可或缺的一部分。此外，所提出的合成展示了银催化的苯甲酸炔丙酯的环化。该教育计划包括通过俄勒冈州立大学 NSF 研究生教育研究生研究培训创新 (NRT IGE) 拨款对研究生进行专业发展培训，以及通过俄勒冈州内一两所其他学校的外展活动进行社区参与。