Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars. Issue 25 (12th June 2018)

• Record Type: Journal Article
• Authors: Malinowski, Maciej; Hensienne, Raphaël; Kern, Nicolas; Tardieu, Damien; Bodlenner, Anne; Hazelard, Damien; Compain, Philippe
• Is Part Of: Organic & biomolecular chemistry. Volume 16:Issue 25(2018)
• Page Start: 4688
• Page End: 4700
• Publication Date: 2018-06-12
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c8ob01065j
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : First examples of a new class of constrained bicyclic iminosugars have been synthesized by a non-classical Dieckmann-like reaction. Abstract : We report herein the development of a stereodivergent route towards polyhydroxylated bicyclic azetidine scaffolds, namely 6-azabicyclo[3.2.0]heptane derivatives. The strategy hinges on a common bicyclic β-lactam precursor, which is forged by way of a rare example of a cationic Dieckmann-type reaction, followed by IBX-mediated desaturation. Substrate-controlled diastereoselective oxidations then allow the divergent preparation of novel iminosugar mimics.