Gamboa Marin, Oscar Javier, Hussain, Nazar, Ravicoularamin, Gokulakrishnan, Ameur, Nassima, Gormand, Paul, Sauvageau, Janelle et Gauthier, Charles 
ORCID: https://orcid.org/0000-0002-2475-2050
(2020).
Total Synthesis of 6-Amino-2,6-dideoxy-alpha-Kdo from d-Mannose
Organic Letters
, vol. 22
, nº 15.
p. 5783-5788.
DOI: 10.1021/acs.orglett.0c01847.
Résumé
3-Deoxy-d-manno-oct-2-ulosonic acid (Kdo) biosynthetic pathway is a promising target in antibacterial drug discovery. Herein, we report the total synthesis of 6-amino-2,6-dideoxy-alpha-Kdo in 15 steps from d-mannose as a potential inhibitor of Kdo-processing enzymes. Key steps of the synthetic sequence involve a Horner-Wadsworth-Emmons reaction for the two-carbon chain homologation followed by either a 6-exo-trig Pd-catalyzed reductive cyclization or a tandem Staudinger/aza-Wittig reaction with concomitant alpha-iminoester reduction, enabling the alpha-stereoselective formation of the Kdo-like six-membered azacyclic ring.
| Type de document: | Article |
|---|---|
| Mots-clés libres: | - |
| Centre: | Centre INRS-Institut Armand Frappier |
| Date de dépôt: | 20 juill. 2021 03:59 |
| Dernière modification: | 15 févr. 2022 17:30 |
| URI: | https://espace.inrs.ca/id/eprint/11584 |
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