Chemistry of renieramycins. Part 12: An improved total synthesis of (卤)-renieramycin G

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• 作者：Masashi Yokoya ; Kimiko Shinada-Fujino ; Saiko Yoshida ; Masahiro Mimura ; Hiroki Takada ; Naoki Saito ; ^{naoki@my-pharm.ac.jp}
• 关键词：Total synthesis ; Marine natural product ; Isoquinoline ; Renieramycin G ; Cytotoxicity
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：3 June, 2012
• 卷：68
• 期：22
• 页码：4166-4181
• 文件大小：568 K

摘要

An improved total synthesis of (卤)-renieramycin G (1g) from readily available 2-hydroxy-3-methyl-4,5-dimethoxybenzaldehyde (7) in 21 steps (6.3%overall yield) is described. The synthesis features the concise construction of a pentacyclic framework using the stereoselective Pictet-Spengler type cyclization reaction of lactam (25) with ethyl diethoxyacetate, followed by the base-catalyzed epimerization of the C-1 stereo center of aldehyde (30a). The results of cytotoxicity studies are also presented.