Divergent Synthesis of Hydro-γ-Carbolines and Multisubstituted Indoles through Grob Fragmentation/Mannich Cyclization

Long Jiang; Yuanyuan Yu; Guang Li; Liansuo Zu

doi:10.1002/asia.201600980

Divergent Synthesis of Hydro-γ-Carbolines and Multisubstituted Indoles through Grob Fragmentation/Mannich Cyclization

Chem Asian J. 2016 Oct 20;11(20):2838-2840. doi: 10.1002/asia.201600980. Epub 2016 Sep 21.

Authors

Long Jiang¹, Yuanyuan Yu¹, Guang Li¹, Liansuo Zu²

Affiliations

¹ School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084, China.
² School of Pharmaceutical Sciences, Tsinghua University, Beijing, 100084, China. zuliansuo@biomed.tsinghua.edu.cn.

PMID: 27558845
DOI: 10.1002/asia.201600980

Abstract

A distinct strategy for the divergent synthesis of hydro-γ-carbolines and multisubstituted indoles is reported. The stereochemical outcomes and a control experiment indicate that the reactions likely proceed through Grob fragmentation/Mannich cyclization rather than a concerted aza-pinacol rearrangement.

Keywords: Grob fragmentation; Mannich cyclization; aza-pinacol rearrangement; hydrocarbolines; indoles.