PERICYCLIC REACTIONS FOR ORGANIC SYNTHESIS

描述：(申请者提供)本建议书主要针对申请者 周环反应在几个化合物合成的新方法中的应用 碳环和杂环有机化合物的重要类别。 第一部分描述了合成五个-的新策略的发展 以及六元芳香族、杂芳族和二氢芳香族体系。 共轭烯炔的分子内(4~2)环加成反应将是 研究并应用于高浓缩多环体系的新路线。 这一过程的杂环变体将被开发出来，从而导致五个和 六元氮和氧杂环。这一点的应用 呋喃并苯二烯类五环二萜化合物的合成 具有蛋白酪氨酸激酶抑制作用的聚酮类海洋天然产物 活性，以及抗病毒药物nothapodytin B的合成 (mappicine酮)也将被检查。 该提案的第二部分描述了开发新的方法，以 共轭不饱和酮的合成及其在新环化中的应用 五元、六元和七元碳环化合物的合成策略 杂环化合物。 提案的第三部分描述了串联丙炔诺酮的应用 重排-不对称逆电子需求分子内乙烯 Diels-Alder策略以一种非常简洁的方法来处理总数 线虫孵化刺激剂甘氨酸乙酯A的合成

DESCRIPTION: (provided by applicant) 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 sixmembered aromatic, heteroaromatic, and dihydroaromatic systems. Intramolecular (4+2) cycloaddition reactions of conjugated enynes will be investigated and employed in new routes to highly condensed polycyclic systems. Heterocyclic variants of this process will be developed leading to five- and six-membered nitrogen and oxygen heterocycles. The application of this chemistry to the synthesis of furanophenalenone diterpenes, pentacyclic 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 development of new methods for the synthesis of conjugated, unsaturated ketenes and their use in new annulation strategies for the synthesis of five-, six-, and seven-membered carbocyclic and heterocyclic compounds. Part III 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 nematode hatching stimulus agent glycinoeclepin A.