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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.

化学系的化学合成项目支持了里奇·G·教授的这个项目。卡特卡特教授和他的合作研究员张教授都是俄勒冈州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聚酮化合物天然产物的化学性质，这些天然产物被称为mandelalides和madeirolides。该提案的总体目标是开发用于构建这些天然产物的创新方法，从而在反应和战略开发方面推进该领域。这些化合物具有良好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）有机化学的专业知识。卡特教授的小组有能力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被纳入该计划。此外，还计划开展外联活动，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的合成策略以及验证新的化学方法学的重要试验平台。所提出的扁桃内酯A-B和madeirolide A的合成推动了现代有机合成的极限。一种新的方法是开发一种可靠的顺式烯烃的不对称二羟基化反应，以快速获得反式二醇，这是这些项目不可或缺的。此外，建议的合成展示银催化环化炔丙基苯甲酸酯。该教育计划包括通过俄勒冈州州立大学的NSF研究生研究生教育培训创新（NRT IGE）赠款为研究生提供专业发展培训，并通过俄勒冈州内的一所或两所额外学校的外联活动进行社区参与。