Stereocontrolled synthesis of polyhydroxylated bicyclic azetidines as a new class of iminosugars
| Autor: | Maciej Malinowski, Nicolas Kern, Raphaël Hensienne, Anne Bodlenner, Damien Hazelard, Damien Tardieu, Philippe Compain |
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| Přispěvatelé: | Laboratoire de chimie moléculaire (LCM), Université de Strasbourg (UNISTRA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Substances naturelles/chimie moléculaire, Université Louis Pasteur - Strasbourg I-Ecole européenne de chimie, polymères et matériaux [Strasbourg]-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'innovation moléculaire et applications (LIMA), Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS) |
| Jazyk: | angličtina |
| Rok vydání: | 2018 |
| Předmět: |
Heptane
Bicyclic molecule 010405 organic chemistry Chemistry Stereochemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Azetidine Cationic polymerization Iminosugar 010402 general chemistry 01 natural sciences Biochemistry 3. Good health 0104 chemical sciences SYBIO chemistry.chemical_compound Physical and Theoretical Chemistry |
| Zdroj: | Organic and Biomolecular Chemistry Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2018, 16, pp.4688-4700. ⟨10.1039/C8OB01065J⟩ |
| ISSN: | 1477-0520 1477-0539 |
| DOI: | 10.1039/C8OB01065J⟩ |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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