| Download | - View supplementary information: Total synthesis of 6-amino-2,6-dideoxy-α-Kdo from d -mannose (PDF, 5.6 MiB)
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| DOI | Resolve DOI: https://doi.org/10.1021/acs.orglett.0c01847 |
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| Author | Search for: Gamboa Marin, Oscar Javier1; Search for: Hussain, Nazar1; Search for: Ravicoularamin, Gokulakrishnan1; Search for: Ameur, Nassima1; Search for: Gormand, Paul1; Search for: Sauvageau, Janelle2, 1, 3; Search for: Gauthier, Charles1ORCID identifier: https://orcid.org/0000-0002-2475-2050 |
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| Affiliation | - Centre Armand-Frappier Santé Biotechnologie, Institut National de la Recherche Scientifique (INRS), 531, boul. des Prairies, Laval, Québec, Canada H7V 1B7
- National Research Council of Canada. Human Health Therapeutics
- National Research Council Canada (NRC), 100 Sussex Drive, Ottawa, Ontario, Canada K1A 0R6
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| Funder | Search for: Fonds de Recherche du Qu?bec - Sant?; Search for: Fonds de Recherche du Qu?bec - Nature et Technologies; Search for: R?seau Qu?b?cois de Recherche sur les M?dicaments; Search for: Fonds De La Recherche Scientifique - FNRS; Search for: Natural Sciences and Engineering Research Council of Canada |
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| Format | Text, Article |
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| Abstract | 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-α-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 α-iminoester reduction, enabling the α-stereoselective formation of the Kdo-like six-membered azacyclic ring. |
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| Publication date | 2020-07-14 |
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| Publisher | American Chemical Society |
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| In | |
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| Language | English |
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| Peer reviewed | Yes |
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| Export citation | Export as RIS |
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| Report a correction | Report a correction (opens in a new tab) |
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| Record identifier | 8f10fc6f-9bb7-4956-ac47-c3eeabd30683 |
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| Record created | 2022-07-19 |
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| Record modified | 2022-07-19 |
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