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