Dépôt numérique

Total Synthesis of 6-Amino-2,6-dideoxy-alpha-Kdo from d-Mannose

Gamboa Marin, Oscar Javier; Hussain, Nazar; Ravicoularamin, Gokulakrishnan; Ameur, Nassima; Gormand, Paul; Sauvageau, Janelle et Gauthier, Charles ORCID logoORCID: 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. pp. 5783-5788. DOI: 10.1021/acs.orglett.0c01847.

Ce document n'est pas hébergé sur EspaceINRS.


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

Gestion Actions (Identification requise)

Modifier la notice Modifier la notice