Parallel synthesis of natural product-like polyhydroxylated pyrrolidine and piperidine alkaloids
| Autor: | Yi-Fan Chang, En-Lun Tsou, Wei-Chieh Cheng, Yi-Wen Pan, Chih-Wei Guo, Ting-Hao Chan |
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| Rok vydání: | 2009 |
| Předmět: |
Pyrrolidines
Substituent Hydroxylation Catalysis Pyrrolidine Inorganic Chemistry Small Molecule Libraries chemistry.chemical_compound Alkaloids Piperidines Drug Discovery Organic chemistry Physical and Theoretical Chemistry Molecular Biology Biological Products Natural product Organic Chemistry General Medicine Combinatorial chemistry Solutions Enantiopure drug chemistry Yield (chemistry) Reagent Organic synthesis Nitrogen Oxides Piperidine Volatilization Information Systems |
| Zdroj: | Molecular diversity. 15(1) |
| ISSN: | 1573-501X |
| Popis: | The preparation of natural product-like polyhydroxylated pyrrolidine and piperidine alkaloids using a combination of solid– and solution-phase organic synthesis is described. The key intermediates, enantiopure five- or six-membered tri-O-benzyl cyclic nitrones, were efficiently prepared on solid support from accessible chiral furanosides and pyranosides, respectively. The substituent diversity was achieved by a diastereoselective addition of a variety of Grignard reagents to the cyclic nitrones in solution-phase synthesis. All reaction steps and work-up procedures were modified to allow the use of automated equipment. A 36-membered demonstration library with three diversity elements (core, configuration, and substituent) was prepared in good yield and purity. |
| Databáze: | OpenAIRE |
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