Development of New Catalytic Reactions for the Synthesis of Natural Products

天然产物合成新催化反应的发展

• 批准号: 1800536
• 负责人: Sarah Reisman
• 金额: $ 45万
• 依托单位: California Institute of Technology
• 依托单位国家: 美国
• 项目类别: Continuing Grant
• 财政年份: 2018
• 资助国家: 美国
• 起止时间: 2018-06-15 至 2022-01-31
• 项目状态: 已结题
• 来源: https://www.nsf.gov/awardsearch/showAward?AWD_ID=1800536&HistoricalAwards=false
• 关键词: Development; New; Catalytic; Reactions; Synthesis

Chemical synthesis plays an important and often rate-limiting role in the fields of molecular medicine, agrochemicals, flavors and fragrances, and materials science. The development and application of new, selective, and efficient processes for the synthesis of functional molecules is therefore a fundamental area of research with broad societal impact. Dr. Sarah Reisman's research funded by this award is investigating new catalytic reactions as key carbon-carbon bond constructions for the synthesis of complex molecules with improved efficiency using the inexpensive and abundant metal, nickel. The research team is developing new reactions that couple different reaction partners as strategic steps in the synthesis of biologically active molecules. These investigations are providing more efficient and sustainable access to molecules with applications in medicine and agrochemicals. Dr. Reisman is engaged in outreach activities focused on improving curriculum for science, technology, engineering and mathematics (STEM) education in the Pasadena Unified School District, with a specific interest in encouraging young women to pursue STEM careers. With funding from the Chemical Synthesis Program of the Chemistry Division, Dr. Sarah Reisman at the California Institute of Technology is developing Ni-catalyzed cross-electrophile coupling (CEC) reactions as strategic reactions for natural product total synthesis. Advances in the synthesis of structurally complex, functional molecules are driven by the development of new synthetic methods to prepare carbon-carbon and carbon-heteroatom bonds, and the incorporation of these methods into increasingly sophisticated synthetic strategies. Dr. Reisman and her research team are developing new Ni-catalyzed double asymmetric reductive alkenylation reactions to prepare macrocycles, and Ni-catalyzed convergent fragment coupling reactions to prepare diterpenoid natural products. This research is contributing fundamental studies of Ni-catalyzed cross- electrophile coupling reactions, and demonstrating how Ni-catalyzed C(sp2)-C(sp3) bond constructions can be incorporated into synthetic strategy. In partnership with the Caltech Center for Teaching, Learning, and Outreach and the Community Science Academy, Dr. Reisman is developing organic chemistry experiments to enhance high school science curriculum in the Pasadena Unified School District (PUSD).This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.

化学合成在分子医学、农用化学品、香料和香料以及材料科学领域中起着重要且通常是限速的作用。因此，开发和应用新的、选择性的和有效的功能分子合成方法是具有广泛社会影响的基本研究领域。由该奖项资助的Sarah Reisman博士的研究正在研究新的催化反应，作为使用廉价和丰富的金属镍合成复杂分子的关键碳-碳键结构，以提高效率。该研究小组正在开发新的反应，将不同的反应伴侣作为合成生物活性分子的战略步骤。这些研究提供了更有效和可持续的获得在医学和农用化学品中应用的分子的途径。Reisman博士从事的外展活动侧重于改善帕萨迪纳联合学区的科学，技术，工程和数学（STEM）教育课程，特别关注鼓励年轻女性追求STEM职业。在化学部化学合成项目的资助下，加州理工学院的Sarah Reisman博士正在开发镍催化的交叉亲电偶联（CEC）反应，作为天然产物全合成的战略反应。结构复杂的功能分子的合成的进展是由制备碳-碳和碳-杂原子键的新合成方法的开发以及将这些方法并入日益复杂的合成策略所驱动的。Reisman博士和她的研究团队正在开发新的Ni催化的双不对称还原烯基化反应以制备大环化合物，以及Ni催化的收敛片段偶联反应以制备二萜类天然产物。本研究为Ni催化的交叉亲电偶联反应的基础研究做出了贡献，并展示了Ni催化的C（sp2）-C（sp3）键结构如何被纳入合成策略。与加州理工学院教学中心和社区科学学院合作，Reisman博士正在开发有机化学实验，以提高帕萨迪纳联合学区（PUSD）的高中科学课程。该奖项反映了NSF的法定使命，并被认为值得通过使用基金会的智力价值和更广泛的影响审查标准进行评估来支持。

项目成果

Synthesis of Noraugustamine and Development of an Oxidative Heck/Aza-Wacker Cascade Cyclization.

• DOI: 10.1021/acs.orglett.2c00948
• 发表时间: 2022-04
• 期刊: Organic letters
• 影响因子: 5.2
• 作者: K. R. Holman;A. M. Stanko;Matthieu J. R. Richter;S. Feng;Mahideremariyam N Gessesse;S. Reisman

Plugging the Leak: Empowering Women in Organic Chemistry

堵住漏洞：赋予有机化学领域女性权力

• DOI: 10.1021/anie202111765
• 发表时间: 2022
• 期刊: Angewandte Chemie
• 作者: Sara E. Dibrell;Karli R. Holman;Sarah E. Reisman
• 通讯作者: Sarah E. Reisman