PDF herunterladen
Synlett
DOI: 10.1055/a-2733-2114
Letter

Enantioselective Synthesis of 2-Azido-norfuranomycin from a D-Glucose-Derived Chiral Synthon

Authors

  • Rajendra Rohokale 

    1   Department of Chemistry, University of Florida, Gainesville, United States (Ringgold ID: RIN3463)
    2   Department of Chemistry, Savitribai Phule Pune University, Pune, India (Ringgold ID: RIN29638)
Weitere Informationen
 als PDF herunterladen Alle Artikel dieser Rubrik
Preview

The enantioselective synthesis of 2-azido-norfuranomycin (11) was accomplished from a D-glucose-derived chiral synthon (4). The absolute configuration at C3 and C4 of synthon 4 corresponds to that of the target molecule, confirming its utility in asymmetric synthesis. Key steps include 1,2-acetonide hydrolysis, oxidative cleavage (NaIO₄), reduction to a 2-azido-3-hydroxy olefin precursor, and ring-closing metathesis (RCM) to form the 3′,4′-dihydrofuran core. The method provides 2-azido-norfuranomycin in high yield and enantiopurity from readily available carbohydrate starting materials. A similar attempt was undertaken to obtain 2-azido-furanomycin 12.



Publikationsverlauf

Eingereicht: 07. Oktober 2025

Angenommen nach Revision: 27. Oktober 2025

Accepted Manuscript online:
27. Oktober 2025

© . Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany