Development of the Vinylogous Pictet–Spengler Cyclization and Total Synthesis of (±)‐Lundurine A. Issue 23 (4th May 2018)

• Record Type: Journal Article
• Authors: Nash, Aaron; Qi, Xiangbing; Maity, Pradip; Owens, Kyle; Tambar, Uttam K.
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 23(2018)
• Page Start: 6888
• Page End: 6891
• Publication Date: 2018-05-04
• Subjects: alkaloids -- cyclization -- Lewis acids -- nitrogen heterocycles -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201803702
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A novel vinylogous Pictet–Spengler cyclization has been developed for the generation of indole‐annulated medium‐sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a prevalent structural motif in many biologically active alkaloids. The strategy has been applied to the total synthesis of (±)‐lundurine A. Abstract : Not just a happy medium : A vinylogous Pictet–Spengler cyclization has been developed for the generation of indole‐annulated medium‐sized rings. The method enables the synthesis of tetrahydroazocinoindoles with a fully substituted carbon center, a structural motif that is prevalent in biologically active alkaloids. The strategy has been applied to the total synthesis of (±)‐lundurine A (see scheme).