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Enantioselective total synthesis of sacrolide A
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2017-09-08 , DOI: 10.1016/j.tetlet.2017.09.017
Tomoyo Mohri , Yusuke Ogura , Ryo Towada , Shigefumi Kuwahara

An enantioselective total synthesis of sacrolide A, an antimicrobial and cytotoxic fourteen-membered macrolactonic oxylipin isolated from an edible freshwater cyanobacterium, has been accomplished from a known carboxylic acid in 20% overall yield by a concise ten-step sequence. The key transformations include chiral oxazolidinone-based diastereoselective installation of two hydroxy-bearing stereocenters, the Horner–Wadsworth–Emmons olefination to construct the full carbon skeleton, and the Shiina macrolactonization to establish the fourteen-membered macrolide structure.



中文翻译:

cro糖内酯A的对映选择性全合成

从食用羧酸蓝藻中分离得到的抗菌剂和具有细胞毒性的十四元大环内脂酰氧杂环丁烯醛对映体的全选择性合成已通过一种简明的十步法从已知羧酸中以20%的总收率完成。关键的转变包括基于手性恶唑烷酮的非对映选择性安装的两个带有羟基的立体中心,霍纳-沃兹沃思-埃蒙斯烯化反应以构建完整的碳骨架,以及什叶纳大内酯化以建立十四元大环内酯结构。

更新日期:2017-09-08
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