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

TETRAHEDRON

卷:69

Article

Ishida, Takayuki¹  Takemoto, Yoshiji¹ 

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Yoshida, Kyoto 60685011, Japan

关键词: Natural product;    Alkaloid;    Samarium diiodide;    Palladium catalysis;    Amidine;   

DOI  :  10.1016/j.tet.2013.04.039

来源: Elsevier

【 摘 要 】

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. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

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