Organoiron Complexes in Organic Synthesis

本研究的重点将是探索环戊二烯酮作为合成联芳基的新途径的化学性质。这一概念将通过将其应用于生物碱希帕丁和相关化合物kalbretorine的合成来进行测试。将环戊二烯酮的共轭加成化学应用于以氢偶氮烯为基础的萜类化合物guanacastepena的合成。此外，将研究一种新的n -羟基乙基吡咯烷氧化环化反应，其中底物在羰基铁催化剂存在下用三甲胺- n -氧化物处理后立体特异性转化为恶唑啉。通过这个奖项，有机和大分子化学项目支持了凯斯西储大学化学系Anthony J. Pearson博士的研究。皮尔逊教授将把他的工作重点放在环戊二烯酮在重要天然产物全合成中的应用上。氧化环化反应也将用于杂环的合成。这项工作有可能对制药业产生更广泛的影响，该项目为有机金属化学应用于有机合成领域的本科生、研究生和博士后提供了一个极好的培训场所。

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.