烯烃的立体选择性氢化反应是构建手性中心的有效方式。然而，对具有不同取代类型的烯烃进行化学选择性还原是一个较困难的课题。我们计划利用CuH物种对不同取代类型双键具有不同活性的特点，开发一种具有化学选择性的烯烃还原反应。我们计划将这个反应与成熟的烯炔偶联反应和环化成醚反应结合，构建具有不同立体构型的3-甲基-2，5-二取代四氢呋喃结构单元，应用于天然产物mandelalides的全合成中。同时，我们将利用Morita-Baylis-Hillman反应从mandelides A骨架构建mandelalides B-E。

Currently, it is difficult to chemoselectively reduce alkenes with different substitution patterns. We propose to take advantage of the different reactivities of CuH species toward different types of alkenes, and develop a general method to reduce alkenes in a chemoselective fashion. We will unite this method with the robust alkene-alkyne coupling and cyclization reactions to construct 3-methyl-2,5-disubstituted tetrahydrofuran rings, and apply it in the total synthesis of mandelalide A. We will further convert mandelalide A to mandelalides B-E via a bio-inspired Morita-Baylis-Hillman reaction.