Total synthesis of antitumor depsipeptide (-)-doliculide
Total synthesis of antitumor depsipeptide (-)-doliculide
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DOI：
10.1021/ol0100069
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发表时间：
2001-02-22
期刊：
影响因子：
5.2
通讯作者：
Liu, CF
中科院分区：
文献类型：
--
作者：
Ghosh, AK;Liu, CF
[图示](-)-Doliculide 是一种有效的抗肿瘤药物，以收敛方式立体选择性合成，关键策略包括立体选择性合成聚酮化合物单元和合成 D-酪氨酸衍生物，然后通过酯化和环酰胺化反应序列组装片段。聚酮化合物片段的合成是通过迭代不对称合成实现的，以立体选择性地安装 1,3-二甲基基团和以不对称环丙烷化反应和Sharpless不对称环氧化反应为关键步骤合成1,3-二醇单元。
[GRAPHICS](-)-Doliculide, a potent antitumor agent, is synthesized stereoselectively in a convergent manner, The key strategy involves a stereoselective synthesis of the polyketide unit and synthesis of the D-tyrosine derivative, followed by assembly of the fragments by an esterification and cycloamidation reaction sequence, The synthesis of the polyketide fragment was achieved by an iterative asymmetric synthesis to install stereoselectively both 1,3-dimethyl groups and the 1,3-diol unit by utilizing asymmetric cycloprapanations and Sharpless asymmetric epoxidations as the key steps.