Innovative Approaches to Macrocyclic Natural Products

化学学部的化学合成项目支持Rich G. Carter教授的这个项目。卡特教授与他的合作研究员张教授均为美国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聚酮类天然产物的化学性质，这些产物被称为扁桃醛类和madeiroides。本提案的总体目标是开发构建这些天然产物的创新方法，从而在反应和策略发展方面推进该领域。这些化合物已显示出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）有机化学方面的专业知识。卡特教授的团队在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方面处于有利地位。专业发展的努力，为学生参与这个项目是整合到该计划。此外，还计划开展外展活动，使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和验证新化学方法的重要试验台。提出的曼德拉内酯A- b和马德拉内酯A的合成突破了现代有机合成的极限。一种新方法是开发一种可靠的顺式烯烃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一部分。此外，所提出的合成展示了银催化的丙炔苯甲酸酯环化反应。该教育计划包括通过俄勒冈州立大学的NSF研究生研究培训创新研究生教育（NRT IGE）资助对研究生进行专业发展培训，以及通过在俄勒冈州另外一到两所学校开展外展活动进行社区参与。

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.