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Synlett
DOI: 10.1055/a-2733-2114
DOI: 10.1055/a-2733-2114
Letter
Enantioselective Synthesis of 2-Azido-norfuranomycin from a d-Glucose-Derived Chiral Synthon
Authors
Abstract
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.
Keywords
Furanomycin - Norfuranomycin - Non-proteinogenic amino acids - Antibiotics - Natural products - Total synthesisPublication History
Received: 07 October 2025
Accepted after revision: 27 October 2025
Accepted Manuscript online:
27 October 2025
Article published online:
20 November 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
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