CSIR-National Chemical Laboratory, Pune-411 008, India.
Org Lett. 2012 Feb 17;14(4):1082-5. doi: 10.1021/ol203466m. Epub 2012 Feb 8.
A concise and highly stereoselective total synthesis of manzacidin B and its congeners has been developed following chelation-controlled syn-epoxidation and Lewis acid catalyzed intramolecular regioselective epoxide ring opening to generate the quarternary amine center. Elaboration of the triol moiety to the target molecule was achieved in good overall yield, representing practical total syntheses of manzacidin B and its congeners. From the XRD, NMR, and analytical data, the correct structure of natural manzacidin B, (4R,5R,6R)-6, was confirmed.
已开发出一种简洁且高度对映选择性的曼沙菌素 B 及其同系物的全合成方法，该方法采用螯合控制的 syn-环氧化和路易斯酸催化的分子内区域选择性环氧化物开环反应生成季铵中心。通过三醇部分的详细研究，以良好的总收率实现了目标分子的目标分子，代表了曼沙菌素 B 及其同系物的实际全合成。通过 XRD、NMR 和分析数据，确定了天然曼沙菌素 B（（4R，5R，6R）-6）的正确结构。
