Synthesis of Heterocyclic Natural Products

一种新的Heck钯催化的 卤乙烯与烯烃分子内偶联将 可开发用于构建各种氮 杂环 该方法允许同时形成C-C 和C-N键，产生双环系统。 基本 方法将进一步探讨，然后应用于 石松属生物碱石松碱的简明合成 螺环生物碱全氢组胺毒素。 的 化学也将扩大到允许形成两个新的 C-C键，导致一系列碳环系统。 这 方法的变化将适用于建设的 假愈创木烷环系统，将是关键的一步， 石松属植物中Magellanine/Paniculatin基团的合成 生物碱以及螺环倍半萜 β-氯米格雷 %%% 有了这个奖项，有机合成计划将支持 Steven M博士的研究。宾夕法尼亚州立大学 大学 这项研究探索了新的分支， 一种新的钯催化反应在构建 通过新的合成方法， 有利于生物化学和医学的研究， 化学工业。

A novel variation of the Heck palladium catalyzed intramolecular coupling of a vinyl halide with an alkene will be developed for construction of a variety of nitrogen heterocycles. The process allows concurrent formation of a C-C and a C-N bond, producing a bicyclic ring system. The basic methodology will be explored further and then applied in concise syntheses of the Lycopodium alkaloid phlegmarine and the spirocyclic alkaloid perhydrohistrionicotoxin. The chemistry will also be extended to allow formation of two new C-C bonds, leading to a range of carbocyclic systems. This methodological variation will be applied to construction of the pseudoguaiane ring system and will be a key step in total syntheses of the magellanine/paniculatin group of Lycopodium alkaloids as well as the spirocyclic sesquiterpene beta-chamigrene. %%% With this award, the Organic Synthesis Program will support the research of Dr. Steven M. Weinreb at Pennsylvania State University. The research explores new ramifications and applications of a new palladium catalyzed reaction to construct complex structures by new synthetic methodology that should benefit research in biochemistry and medicine, as well as in the chemical industry.