University of Vienna, Institute of Organic Chemistry, Währinger Strasse 38, 1090 Wien, Austria.
Org Lett. 2009 Mar 5;11(5):1151-3. doi: 10.1021/ol9000137.
The first total synthesis of the sesquiterpenoid valerenic acid, a constituent of Valeriana officinalis, is described. The compound is a potent modulator of the GABA(A) receptor and may thus be useful in the treatment of various dysfunctions of the central nervous system. The synthesis is enantio-, diastereo-, and regiocontrolled and utilizes an enyne-RCM, a metal-coordinated Diels-Alder reaction, a hydroxy-directed Crabtree hydrogenation, and a Negishi methylation as key steps.
首次全合成了缬草烯酸，这是缬草（Valeriana officinalis）的一种成分。该化合物是 GABA(A) 受体的有效调节剂，因此可能对中枢神经系统的各种功能障碍有用。该合成是对映体、非对映体和区域控制的，并利用烯炔-RCM、金属配位的 Diels-Alder 反应、羟基导向的 Crabtree 氢化和 Negishi 甲基化作为关键步骤。
