A dipolar cycloaddition approach toward the kopsifoline alkaloid framework

TETRAHEDRON

卷:63

Article; Proceedings Paper

Hong, Xuechuan¹  France, Stefan¹  Padwa, Albert¹ 

[1] Emory Univ, Dept Chem, Atlanta, GA 30322 USA

关键词: diazoimide;    synthesis;    indole;    cycloaddition;    rhodium(II);    kopsifoline;    alkaloid;   

DOI  :  10.1016/j.tet.2007.01.064

来源: Elsevier

【 摘 要 】

Using a metal-catalyzed domino reaction as the key step, the heterocyclic skeleton of the kopsifoline alkaloid family was constructed by a 1,3-dipolar cycloaddition of a carbonyl ylide dipole derived from a Rh(II)-catalyzed reaction of a diazo ketoester across the indole pi-bond. Ring opening of the resulting 1,3-dipolar cycloadduct followed by a reductive dehydroxylation step resulted in the formation of a critical silyl enol ether necessary for the final F-ring closure of the kopsifoline skeleton. (C) 2007 Elsevier Ltd. All rights reserved.

【 授权许可】

Free