Asymmetric Synthesis of Spiroketal, Spiroether, and Oxabicycle Building Blocks via Stereoselective Spiro- and Bicycloannulation of 2-Hydroxy Dihydropyrans
| Autor: | Hans-Joachim Gais, Jan Runsink, Michal Lejkowski, Prabal Banerjee |
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| Rok vydání: | 2008 |
| Předmět: |
Glycosylation
Molecular Structure Sulfur Compounds Chemistry Stereochemistry Organic Chemistry Enantioselective synthesis Stereoisomerism Alkenes Prins reaction Hydroxylation Metathesis Biochemistry Oxygen Spiroether Cyclization Ethers Cyclic Spiro Compounds Stereoselectivity Imines Physical and Theoretical Chemistry Furans Hydrogen Pyrans |
| Zdroj: | Organic Letters. 10:2713-2716 |
| ISSN: | 1523-7052 1523-7060 |
| DOI: | 10.1021/ol800854s |
| Popis: | A modular asymmetric synthesis of spiroketal, spiroether, and oxabicycle building blocks is described based on the spiro- and bicycloannulation of alpha-hydroxy dihydropyrans, which were obtained from sulfoximine-substituted homoallylic alcohols. Key steps of the syntheses are stereoselective Ferrier-type O- and C-glycosidation, ring-closing metathesis, and stereoselective Prins cyclization. |
| Databáze: | OpenAIRE |
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