Total stereocontrolled synthesis of a novel pyrrolizidine iminosugar
| Autor: | Martina De Angelis, Federica Lizzio, Andrea D'Annibale, Sonia Agostinelli, Alessandra Ricelli, Roberto Antonioletti, Giuliana Righi, Ilaria Ben Rondam, Ludovica Primitivo, Luciano Bonanni, Carla Sappino |
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| Rok vydání: | 2022 |
| Předmět: |
Asymmetric dihydroxylation
Azidolysis Iminosugars Pyrrolizidine iminosugars Stereocontrolled synthesis Organic Chemistry Iminosugar Epoxide Stereoisomerism General Medicine Biochemistry Combinatorial chemistry Pyrrolidine Analytical Chemistry chemistry.chemical_compound chemistry Dihydroxylation Biological property Pyrrolizidine Epoxy Compounds Stereoselectivity Pyrrolizidine Alkaloids |
| Zdroj: | Carbohydrate Research. 511:108484 |
| ISSN: | 0008-6215 |
| Popis: | Herein we describe a versatile approach to the pyrrolizidine alkaloids skeleton by tailoring our original strategy already used for the pyrrolidine iminosugars synthesis. The key steps are the regio- and stereoselective azidolysis of the suitable chiral vinyl epoxide and then asymmetric dihydroxylation of the corresponding azido alcohol by using (DHQ)2AQN as the ligand. Further optimized elaborations addressed to the closure of the two rings allowed us to achieve the target iminosugar with complete stereocontrol. The wide range of pyrrolizidine iminosugars’ biological properties make them a key focus of new drug research and therefore the development of synthetic strategies for obtaining them is of decisive importance. |
| Databáze: | OpenAIRE |
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