Practical Syntheses of Proposed and Revised Manzacidin B and Their Congeners

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.

采用螯合控制下的合成-环氧化和路易斯酸催化的分子内区域选择性环氧环开环，成功开发了一种对曼扎西丁B及其同系物进行高度立体选择性的全合成方法。该合成方法通过将三醇基团转化为目标分子，实现了良好的总体收率，代表了曼扎西丁B及其同系物的实用全合成。通过X射线衍射、核磁共振和解析数据的分析，确认了天然曼扎西丁B（4R,5R,6R）-6的正确结构。