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Stereoselective Synthesis of Key Skeleton of Mohangic Acids A-E
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2024-06-06 , DOI: 10.1002/ejoc.202400365
Joyanta Mondal 1 , Sandip Guchhait 2 , Himangshu Sharma 2 , Rajib Kumar Goswami 3
Affiliation  

The key skeleton that could allow to access structurally intriguing mohangic acids A-E has been synthesized in stereoselective manner. The salient features of this synthesis include Evans syn-aldol reaction to construct the C-11 and C-12 centers, HWE olefination to construct C14-C15 bond, Evans asymmetric methylation to install C-14 center and Crimmins acetate aldol to generate C-15 center whereas Wittig and Takai olefinations to prepare the C8-C9 & C6-C7 alkenes, respectively, and Heck reaction to couple C1-C5 & C6-C17 segments of the molecules. The developed route is highly modular and useful for accessing diverse natural product like molecules for future investigations

中文翻译:


莫汉酸A-E关键骨架的立体选择性合成



以立体选择性方式合成了能够获得结构上有趣的莫汉酸 A-E 的关键骨架。该合成的显着特征包括Evans顺醛醇反应构建C-11和C-12中心、HWE烯化反应构建C14-C15键、Evans不对称甲基化安装C-14中心和Crimmins乙酸羟醛反应生成C- 15中心,而Wittig和Takai烯化分别制备C8-C9和C6-C7烯烃,以及Heck反应来偶联分子的C1-C5和C6-C17片段。开发的路线是高度模块化的,可用于获取多种天然产物(如分子)以进行未来的研究
更新日期:2024-06-07
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