Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 16, Issue 25, Pages 4688-4700Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c8ob01065j
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Funding
- CNRS [UMR 7042]
- University of Strasbourg
- International Centre for Frontier Research in Chemistry (icFRC)
- French Department of Research
- National Science Center of Poland (Etiuda doctoral fellowship) [UMO-2016/20/T/ST5/00188]
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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 -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.
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