Development of Pummerer-Based Oxidative Cyclization Chemistry for Natural Products Synthesis

本研究的重点是开发利用Pummerer氧化重排法制备3,3-螺旋环-杂环及相关体系的方法。具体靶点包括3,3-螺环氧吲哚、3,3-螺环苯并呋喃酮、5,5-螺环恶唑烷酮和5,5-螺环咪唑啉酮。这些化合物为制备大量具有有趣生物学特性的天然产物提供了模型。有了这个奖项，有机和大分子化学项目支持宾夕法尼亚州立大学化学系的肯·s·费尔德曼博士的研究。费尔德曼教授将专注于开发选择性氧化环化的合成应用。通过这种方式，将增加杂环氧化环化化学的知识体系，并使用该方法，合成用于制备天然产物的模型化合物。该项目将对制药业产生更广泛的影响，并将为本科生（其中一些来自代表性不足的少数群体）和研究生的培训提供一个极好的场所。

The focus of this research is concerned with developing methods for the preparation of 3,3-spirocycle-heterocycle and related systems by the use of the Pummerer oxidative rearrangement. Specific targets include 3,3-spyrocyclic oxindole, 3,3-spirocyclic benzofuranone, 5,5-spirocyclic oxazolidinone and 5,5-spirocyclic imidazolinone. These compounds serve as models for the preparation of a large number of natural products having interesting biological properties.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Ken S. Feldman of the Department of Chemistry at Pennsylvania State University. Professor Feldman will focus his research efforts on developing synthetic applications of selective oxidative cyclization. In this way, the body of knowledge on heterocyclic oxidative cyclization chemistry will be augmented and using the methodology, syntheses of model compounds for the preparation of natural products will be carried out. The project has broader impacts for the pharmaceutical industry and, will afford an excellent venue for the training of undergraduates, some from underrepresented minority groups, and graduate students.