Journal
TETRAHEDRON
Volume 67, Issue 49, Pages 9555-9564Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.10.008
Keywords
1,3-Dipolar cycloaddition; Iminosugar; Indolizidine; Glycosidase; Triazole
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Funding
- Ministry of Research and University (MiUR-Rome, Italy)
- Ministerio de Educacion y Ciencia of Spain [CTQ2004-00649/BQU, CTQ2008-01565/BQU]
- Junta de Andalucia [FQM-345]
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Diversity-oriented synthesis of derivatives of the potent glycosidase inhibitor lentiginosine can be achieved in an efficient and versatile way by two modular approaches on key intermediates. After assembling the indolizidine ring system through 1,3-dipolar cycloaddition of a dihydroxylated pyrroline N-oxide with 4-butenol followed by elaboration of the isoxazolidine moiety, the 7-amino and 7-azido derivatives synthesized can be conjugated with functionalised chains by coupling, respectively, with an amino acid, or an alkyne in copper-catalyzed Huisgen cycloadditions. (C) 2011 Elsevier Ltd. All rights reserved.
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