Enantioselective Synthesis via Allylic Sulfide Anions and Carbohydrate-Derived Chirons (Chemistry)

研究目标是：（1）优化 烯丙基硫醚缩合反应参数 阴离子与环氧化物和随后的产物转化 E，E-2，4-双烯醇;（2）丙二酸酯与 一种衍生自D-葡萄糖的烯酮， （3）制备亲电手性试剂和亲电手性试剂， 来自D-阿拉伯糖的亲核手性配体;和 (4)最终 将这些方法纳入一个模块化办法， 15-氧代美登木素生物碱的对映选择性合成。 一个关键因素 本研究的重点是培养高素质的本科生 为科学，以及，更好地准备他们的研究生 研究化学。 该项目将开发新的合成方法， 制备非常复杂的生物碱， 理论和医学价值。

The investigation objectives are: (1) the optimization of reaction parameters for the condensation of allylic sulfide anions with epoxides and subsequent conversion of the products into E,E-2,4-pentadienols; (2) Michael addition of malonates to an enone derived from D-glucose and subsequent transformations thereof; (3) the preparation of an electrophilic chiron and a nucleophilic chiron from D-arabinose; and (4) the eventual integration of these methodologies into a modular approach to the enantioselective synthesis of 15-oxomaytansinoids. A key element of this study is the training of talented undergraduate students for science, as well as, better preparing them for graduate studies in chemistry. This project will develop new synthetic methods directed at the preparation of very complex alkaloids that are of potential theoretical and medical value.