Total synthesis of (+)-sinefungin

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6175-6182

  Ghosh, Arun K ^a   Liu, Wenming ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SINEFUNGIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029815590     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960670g     Document Type: Article

References (49)

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14. For total synthesis, see; (a) Maguire, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1990, 55, 948. (b) Buchanan, J. G.; Flinn, A.; Mundill, P. H.; Wightman, R. H. Nucleosides Nucleotides 1986, 5, 313. (c) Geze, M.; Blanchard, P.; Fourrey, J. L.; Robert-Gero, M. J. Am. Chem. Soc. 1983, 103, 7638. (d) Mock, G. A.; Moffat, J. G. Nucleic Acids Res. 1982, 10, 6223. For synthesis of 6-deaminosinefungin derivatives, see; Peterli-Roth, P.; Maguire, M. P.; Leon, E.; Rapoport, H. J. Org. Chem. 1994, 59, 4186.
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39. For HPLC analysis, a mixture of C-9 diastereomers were prepared by hydrogenation of the mixture of enamides 14 and 15 over 5% Pd-C in methanol under a hydrogen filled balloon at 23°C for 8 h. This has afforded a mixture (60:40) of 19 and 22 in 78% isolated yield.
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41. Daicel OD column was purchased from Chiral Technologies, 730 Springdale Dr., Exton, PA.
42. Isocratic normal phase HPLC analysis on a Chiralcel OD column (25 cm) using 10% 2-propanol in hexane as eluant (flow rate: 1.1 mL/min) and UV detection at 254 nm indicated that both diastereomers could be cleanly separated. Retention times for diastereomer 19: 17.10 min and diastereomer 22: 20.67 min.
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46. 4-catalyzed adenosylation reaction of the anomeric acetates containing C-6 azide and C-9 amino acid protected as p-toluenesulfonamide and tert-butyl ester.
47. 2O) of a crude sample of 30 indicated the absence of benzoyl, acetyl, and ethyl ester groups.
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