PERICYCLIC REACTIONS FOR ORGANIC SYNTHESIS

本文重点介绍了周环反应在有机合成中的应用。 合成几类重要化合物的新方法 碳环和杂环有机化合物。 第一部分描述了综合的新策略的发展 五元和六元芳香族、杂芳族和 二氢芳香族体系。分子内[4 2]环加成反应 结合酶的反应将被研究并应用于 通向高度浓缩多环系统的新路线。杂环 这一过程的变种将被开发出来，导致替代 吡啶、二氢异苯并呋喃和异吲哚。技术的应用 这种化学对合成五元聚酮海洋化合物的影响 具有蛋白酪氨酸激酶抑制活性的天然产物和 抗病毒药物Nothapodytin B(Mappicine)的合成 酮)也将被检查。 提案的第二部分描述了串联的应用。 丙叉重排-不对称逆电子需求 分子内乙烯基烯Diels-Alder策略 线虫孵化全合成的简明方法 刺激剂甘氨酸乙酯A 提案的第三部分描述了一种新方法的开发 用于合成(三烷基硅基)乙烯基酮和炔基酮以及 这些化合物在环加成新工艺中的应用 导致五元和六元碳环和杂环 化合物。

This proposal focuses on the application of pericyclic reactions in new methodology for the synthesis of several important classes of carbocyclic and heterocyclic organic compounds. Part I describes the development of new strategies for the synthesis of five- and six- membered aromatic, heteroaromatic, and dihydroaromatic systems. Intramolecular [4+2] cycloaddition reactions of conjugated enzymes will be investigated and employed in new routes to highly condensed polycyclic systems. Heterocyclic variants of this process will be developed leading to substituted pyridines, dihydroisobenzofurans, and isoindoles. The application of this chemistry to the synthesis of pentacylic polyketide marine natural products with protein tyrosine kinase inhibitory activity and to the synthesis of the antiviral agent nothapodytine B (mappicine ketone) will also be examined. Part II of the proposal describes the application of a tandem propargylic rearrangement-asymmetric inverse electron-demand intramolecular vinylallene Diels-Alder strategy in an exceptionally concise approach to the total synthesis of the nematod hatching stimulus agent glycinoeclepin A. Part III of the proposal describes the development of a new method for the synthesis of (trialkylsilyl) vinyl- and alkynylketens and application of these compounds in new cycloadditions processes leading to five- and six-membered carbocyclic and heterocyclic compounds.