Maulide Nuno, Souris Caroline, Frébault Frédéric, Luparia Marco, Audisio Davide
University of Vienna Institute of Organic Chemistry Währinger Straße 38 A-1090 Vienna, Austria.
Chimia (Aarau). 2014;68(4):248-51. doi: 10.2533/chimia.2014.248.
We have reported a direct and stereoselective synthesis of functionalized dienoic carboxylates from the simple bicyclic lactone 1. The use of oxygen- or nitrogen-based nucleophiles in a domino allylic alkylation/4π-electrocyclic ring opening affords reliable access to dienes with interesting functionalities. Alternatively, halide substitution offers synthesis of other classes of functionalized dienoic acids. Herein, we demonstrate the utility of such dienoic products as key building blocks in various transformations as well as natural product synthesis.
我们已经报道了从简单的双环内酯1直接立体选择性合成官能化二烯酸酯的方法。在多米诺烯丙基烷基化/4π-电环化开环反应中使用氧或氮亲核试剂，能够可靠地获得具有有趣官能团的二烯。另外，卤化物取代反应可用于合成其他类型的官能化二烯酸。在此，我们展示了此类二烯产物作为关键结构单元在各种转化反应以及天然产物合成中的应用。
