Synthesis of two chiral octahydroindole scaffolds for drug discovery. Issue 9 (3rd March 2016)

• Record Type: Journal Article
• Authors: Sydnes, Magne O.; Van Le, Phuc; Olschimke, Jens; Healy, Peter C.; Garavelas, Agatha; Tajabadi, Fatemeh Mazraati; Pedro, Liliana; Quinn, Ronald J.; Jenkins, Ian D.
• Is Part Of: Tetrahedron. Volume 72:Issue 9(2016)
• Page Start: 1225
• Page End: 1228
• Publication Date: 2016-03-03
• Subjects: Natural-product -- Scaffold -- Drug-discovery -- Synthesis -- Octahydroindole; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.01.018
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: There are over one thousand natural products that contain the octahydroindole scaffold, which can be considered a biologically validated starting point for the design of compound libraries. Two chiral octahydroindole scaffolds have been synthesized in multigram quantities in two steps from a readily available indoline. They contain either one or two amino groups (one Boc-protected) and a protected carboxylic acid group, and have been designed for ease of conversion to a lead generation library. The structures of both scaffolds have been established unequivocally by single crystal X-ray structure determination. Graphical abstract: Two novel, crystalline, highly functionalized, homochiral scaffolds were efficiently constructed in multigram quantities from readily available starting points.