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Volumn , Issue 12, 2007, Pages 1851-1856

Stereocontrolled photocyclization of 1,2-diketones applied to carbohydrate models: A new entry to C-ketosides

Author keywords

Diastereoselectivity; Glycosides; Memory effect; Photochemistry; Spiro compounds

Indexed keywords

1 GLYCOSYL 2,3 BUTANEDIONE DERIVATIVE; 1 HYDROXY 1 METHYL 2 CYCLOBUTANONE; 1 HYDROXY 1 METHYL 5 OXASPIRO[3.5]NONAN 2 ONE; 1,2 DIKETONE DERIVATIVE; CARBOHYDRATE; KETONE DERIVATIVE; KETOSIDE DERIVATIVE; PHOTOSENSITIZING AGENT; UNCLASSIFIED DRUG;

EID: 34547699270     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984523     Document Type: Article
Times cited : (22)

References (39)
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    • The numbering system used throughout the text is based on 1-methyl-2,3-alkanedione and corresponds to that depicted in structures of Table 1 and Schemes 1-3.
    • The numbering system used throughout the text is based on 1-methyl-2,3-alkanedione and corresponds to that depicted in structures of Table 1 and Schemes 1-3.
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    • The 1,2-diketones 1-4 shown in Table 1 were prepared from their corresponding alkynes via ozonolysis: (a) Favino, T. F.; Fronza, G.; Fuganti, C.; Fuganti, D.; Graselli, P.; Mele, A. J. Org. Chem. 1996, 61, 8975.
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    • General Procedure for the Photocyclization of 1,2-Diketones The corresponding 1,2-diketone placed in a Pyrex vessel with or without the indicated solvent (approx. 0.05 M) was irradiated with sunlight or a UV lamp, placed at 10 cm distance from the flask, until the reaction turned colorless. If it proceeded, the mixture was concentrated in vacuo. Column or Chromatotron® chromatography of the residue (hexanes-EtOAc mixtures) afforded the cyclic compounds. General Procedure for the Photocyclization of 1,2-Diketones with Photosensitizers The corresponding 1,2-diketone (0.038 mmol) and photosensitizer (benzophenone or pyrene; 0.5 mmol) was dissolved in CDCl3 (1 mL) and placed in a NMR tube. The reaction mixture was irradiated with an UV lamp, placed at 10 cm distance from the flask, until complete conversion and the solvent was removed under vacuum. The reaction was monitored by 1H NMR. Chromatotron® chromatography of the residue with hexanes to r
    • 3): δ = 1.37 (3 H, s), 2.62 (1 H, d, J = 17.5 Hz), 3.31 (1 H, d, J = 17.5 Hz), 3.50 (1 H, m), 3.55 (1 H, m), 3.60 (1 H, t, J = 8.8 Hz), 3.70 (1 H, d, J = 8.6 Hz), 3.61-3.79 (2 H, m), 4.44 (1 H, d, J = 11.7 Hz), 4.46 (1 H, d, J = 11.8 Hz), 4.53 (1 H, d, J = 10.8 Hz), ...


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