Rapid synthesis of the 7-deoxy zaragozic acid core
Rapid synthesis of the 7-deoxy zaragozic acid core
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DOI：
10.1021/ol0169980
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发表时间：
2002-01-24
期刊：
影响因子：
5.2
通讯作者：
Lachicotte, RJ
中科院分区：
文献类型：
--
作者：
Calter, MA;Zhu, C;Lachicotte, RJ
[图表]我们已经开发了7-脱氧萨拉戈萨酸核心的有效合成。合成开始于Feist-Benary反应，该反应组装核的多羧酸部分的所有三个碳。该反应之后是高度非对映选择性的羟醛和二羟基化反应，其设置核心的剩余立体中心。该合成以内缩醛氧化和内酯醇解/缩酮形成反应完成，以构建核心的双环系统。
[GRAPHICS]We have developed an efficient synthesis of the 7-deoxy zaragozic acid core. The synthesis begins with a Feist-Benary reaction that assembles all three carbons of the polycarboxylic acid portion of the core. This reaction is followed by highly diastereoselective aldol and dihydroxylation reactions that set the remaining stereocenters of the core. The synthesis finishes with lactol oxidation and lactone alcoholysis/ketal formation reactions to construct the bicyclic ring system of the core.