Electrochemical Chlorination of Physcion - An Approach to Naturally Occurring Chlorinated Secondary Metabolites of Lichens
作者:Dragana Stevanović、Ivan Damljanović、Mirjana Vukićević、Nedeljko Manojlović、Niko S. Radulović、Rastko D. Vukićević
DOI:10.1002/hlca.201100011
日期:2011.8
The electrochemical chlorination of physcion (=1,8‐dihydroxy‐3‐methoxy‐6‐methylanthracene‐9,10‐dione; 1) in AcOH and CH2Cl2 was investigated by cyclic voltammetry and prep.‐scale electrolysis. This approach provided access to a number of diverse biologically and pharmacologically interesting chlorinated secondary metabolites of lichen. Unlike the only previous literature report on the ‘classical’ chlorination
通过循环伏安法和制备规模的电解研究了physcion (= 1,8-二羟基-3-3-甲氧基-6-甲基蒽-9,10-二酮; 1)在AcOH和CH 2 Cl 2中的电化学氯化。这种方法使人们能够接触到许多生物学上和药理学上有趣的地衣的氯化次生代谢产物。不同于以前有关“经典”的十氯磷的文献报道(1),该文献允许制备4-氯五氯酮(2b),4,5-二氯五氯甲烷(3b)和2,4,5-三氯五氯甲烷(4)。 ,本程序还得到了脆蛋白(= 2-氯physcion; 2a)和2,4-二氯physcion(=3a),以及先前获得的2b,3b和4。除2a外,所有这些化合物均通过柱色谱和中压液相色谱(MPLC)进行分离,并通过光谱数据进行表征。用2F⋅mol的制备电解-1在AcOH和10F⋅mol电荷消耗-1在CH 2氯2可以具有实际效用的合成中,由于如此得到的产物混合物可以通过柱色谱法容易地分级,得到纯的2b和4,