Organoiron Complexes in Organic Synthesis

本研究的重点将是探索环烯酮的化学作为一种新的方法来合成联芳基。 这个概念将通过将其应用于生物碱希帕定和相关化合物卡勃托林的合成来进行测试。将通过应用于guanacastepene A（一种基于氢化甘菊环的萜类化合物）的合成来探索环己烯酮的共轭加成化学。 此外，还将研究一种新的N-羟乙基吡咯烷的氧化环化反应，即在羰基铁催化剂的存在下，通过使用三甲基胺-N-氧化物处理，将底物立体定向地转化为恶唑啉。有了这个奖项，有机和大分子化学计划将支持凯斯西储大学化学系的Anthony J. Pearson博士的研究。 皮尔逊教授将把他的工作重点放在环己烯酮在重要天然产物的全合成方面的应用上。 氧化环化反应也将被开发用于杂环的合成。这项工作有可能在制药行业产生更广泛的影响，该项目是在有机金属化学应用于有机合成领域培训本科生、研究生和博士后的绝佳场所。

The focus of this research will be to explore the chemistry of cyclopentadienones as a new approach to biaryl synthesis. The concept will be tested by applying it to the synthesis of the alkaloid hippadine, and the related compound kalbretorine. The conjugate addition chemistry of cyclopentadienones will be explored by application to the synthesis of guanacastepene A, a hydroazulene based terpenoid. Further, a new oxidative cyclization of N-hydroxyethylpyrrolidines, in which the substrate is converted stereospecifically to an oxazoline by treatment with trimethylamine-N-oxide in the presence of an iron carbonyl catalyst, will be examined.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Anthony J. Pearson in the Department of Chemistry at Case Western Reserve University. Professor Pearson will focus his work on the use of cyclopentadienones in the context of the total synthesis of important natural products. Oxidative cyclization reactions will also be developed for the synthesis of heterocycles. The work has potential for broader impact in the pharmaceutical industry and the project serves as an excellent venue for the training of undergraduates and graduate students and postdoctorals in the area organometallic chemistry applied to organic synthesis.