Addition of Lithiated 1,3-Dithiane and Nitronate to Sugar-Derived Imines: Synthesis of Homoiminosugars and Pipecolic Acid Analogues
The one-pot two-step stereoselective synthesis of 1,2-<i>trans</i>-1-<i>C</i>-1,3-dithian-2-yl and 1,2-<i>cis</i>-1-<i>C</i>-nitromethyl iminosugars from sugar lactams is disclosed, exploiting Schwartz's reagent triggered amide to imine reduction followed by Corey-Seebach or nitro-Mannich-mediated functionalizations. Processing of the dithiane moiety provided the naturally occurring β-HNJ and α-HMJ homoiminosugars, while processing of the nitromethyl group gave access to α-HNJ and pipecolic acid derivatives. Epimerization of this function was also successfully examined. Final hydrogenolysis furnished a set of known and new glycomimetics, amongst which two compounds displayed potent glycosidase inhibition.
Authors
- Van-Thanh Tran (ORCID: https://orcid.org/0000-0002-4976-0436)
- Jérôme Marrot (ORCID: https://orcid.org/0000-0002-5351-4908)
- Yves Blériot (ORCID: https://orcid.org/0000-0002-3209-9282)
- Isabelle Gillaizeau (ORCID: https://orcid.org/0000-0002-7726-3592)
- Nicolas Auberger (ORCID: https://orcid.org/0000-0002-2076-2112)
- Cyril Nicolas (ORCID: https://orcid.org/0000-0002-3748-2205)
- Suzuka Yamamoto
- Kosuke Yoshimura (ORCID: https://orcid.org/0000-0001-6420-1109)
- Atsushi Kato (ORCID: https://orcid.org/0000-0001-8022-196X)
- Jérôme Désiré (ORCID: https://orcid.org/0000-0003-1076-3610)
Institutions
- Université d'Orléans (FR)
- Centre National de la Recherche Scientifique (FR)
- Université de Poitiers (FR)
- Institut de Chimie des Milieux et des Matériaux de Poitiers (FR)
- Institut de Chimie Organique et Analytique (FR)
- Toyama University Hospital (JP)
- Institut Lavoisier de Versailles (FR)
- University of Toyama (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-09
- DOI
- https://doi.org/10.1021/acs.orglett.5c01061
- Primary Topic
- Carbohydrate Chemistry and Synthesis
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- European Commission
- Agence Nationale de la Recherche
- Japan Society for the Promotion of Science
- European Regional Development Fund