Synthesis of enantiopure C-glycosides and pseudo C-glycosides. Lewis acid mediated cleavage of [3.3.1] oxabicyclic lactones

Synlett

Volumn , Issue 7, 1999, Pages 1041-1044

  Gaertzen, Oliver ^a   Misske, Andrea M ^a   Wolbers, Peter ^a   Hoffmann, H M R ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Anomeric activation; Asymmetric synthesis; Bicyclic lactones; C glycosides; Solvent effect

Indexed keywords

GLYCOSIDE; LACTONE; REDUCING AGENT; SOLVENT;

ARTICLE; CHEMICAL MODIFICATION; CIS TRANS ISOMERISM; COVALENT BOND; PARTIAL DRUG SYNTHESIS;

EID: 0032800210     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2752     Document Type: Article

References (41)

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31. 3, DCM, rt, 15 h. For preparation of lactones 1, 4-8 see refs. 3h and 1I.
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40. 4. The crude product was further purified by short column chromatography to yield the C-glycosidic acid 3A (122 mg, 0.308 mmol, 95%).
41. 3. The trans geometry of 3A was confirmed by 500 MHz NOESY experiments.