Formal synthesis of 6-deoxyerythronolide B
Formal synthesis of 6-deoxyerythronolide B
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DOI：
10.1021/ol0607241
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发表时间：
2006-05-11
期刊：
影响因子：
5.2
通讯作者：
Slade, DJ
中科院分区：
文献类型：
--
作者：
Crimmins, MT;Slade, DJ
以丙醛为起始原料，经23步线性反应，实现了6-脱氧阿糖胞苷B碳骨架的对映选择性合成。合成依赖于一个迭代的方法，采用不对称的酰基噻唑烷酮丙酸酯羟醛缩合反应，建立八个9立体中心。在C6处的剩余立体异构中心通过使用复合烷基碘的Myers烷基化来设置。
The enantioselective synthesis of the carbon skeleton of 6-deoxyerythronolide B has been achieved in 23 linear steps from propionaldehyde. The synthesis relies on an iterative approach employing an asymmetric acyl-thiazolidinethione propionate aldol reaction to establish eight of nine stereogenic centers. The remaining stereogenic center at C6 was set through a Myers alkylation employing a complex alkyl iodide.