Synthetic study of perophoramidine: construction of pentacyclic core structure via SmI₂-mediated reductive cyclization

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• 作者：Takayuki Ishida ; Yoshiji Takemoto ; ^{takemoto@pharm.kyoto-u.ac.jp}
• 关键词：Natural product ; Alkaloid ; Samarium diiodide ; Palladium catalysis ; Amidine
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：10 June, 2013
• 年：2013
• 卷：69
• 期：23
• 页码：4517-4523
• 全文大小：696 K

文摘

An intramolecular SmI₂-mediated reductive cyclization of carbodiimides and unsaturated lactams was applied to functionalized substrates bearing tetrasubstituted olefins. The reaction afforded arylated spiro-2-iminoindolines in high yield. Although the stereochemistry of the product was different from the desired one, the optimized palladium-catalyzed aryl amidination realized the isomerization and C-N bond formation in a single step and resulted in efficient construction of pentacyclic core of perophoramidine synthetically equivalent to the Rainier's intermediate.