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Synthetic studies towards lagunamide C: Polyketide assembly investigations
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2018-01-04 , DOI: 10.1016/j.tetlet.2017.12.083
Anthony Fatino , Chelsea Weese , Salvador Valdez , Alberto Jiménez-Somarribas , Ryan J. Rafferty

Lagunamide C is a depsipeptide natural product with low nM cytotoxicity towards numerous cancer cell lines. Synthetically, it is disconnected to a pentapeptide backbone and polyketide unit that possesses four stereogenic centers, of which two of centers are in question (C38 & 40). Our model system highlights a high-selective aldol addition via a Crimmin’s auxiliary setting the C40 ester linkage, and a non-facially selective cyclopropanation with subsequent ring opening for the installation of the C38 methyl center.



中文翻译:

Lagunamide C的合成研究:聚酮化合物的组装研究

Lagunamide C是一种十肽天然产物,对多种癌细胞具有低nM细胞毒性。综合而言,它与拥有四个立体生成中心的五肽主链和聚酮化合物单元断开连接,其中两个中心存在问题(C38和40)。我们的模型系统突出显示了通过Crimmin的辅助设置C40酯键进行的高选择性羟醛加成,以及非表面选择性的环丙烷化以及随后的C38甲基中心安装的开环。

更新日期:2018-01-04
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