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Volumn 121, Issue 49, 1999, Pages 11375-11383

Total synthesis and comparative evaluation of luzopeptin A-C and quinoxapeptin A-C

Author keywords

[No Author keywords available]

Indexed keywords

LUZOPEPTIN A; QUINOXALINE DERIVATIVE; RNA DIRECTED DNA POLYMERASE;

EID: 0033572757     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993019e     Document Type: Article
Times cited : (49)

References (59)
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    • EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOAt = 1-hydroxy-7-azabenzotriazole; DCC = 1,3-dicydohexylcarbodiimide; DMAP = 4-dimethylaminopyridine; HOBt = 1-hydoxybenzotriazole; SES = 2-(trimethylsilyl)ethylsulfonyl
    • EDCI = 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; HOAt = 1-hydroxy-7-azabenzotriazole; DCC = 1,3-dicydohexylcarbodiimide; DMAP = 4-dimethylaminopyridine; HOBt = 1-hydoxybenzotriazole; SES = 2-(trimethylsilyl)ethylsulfonyl.
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    • note
    • Analysis of the starting ester revealed that 23 existed as a mixture (94:6) of enatiomers. The major (S)-enantiomer of 23 was chromatographically purified on a semipreparative Diacel Chiracel OD column (10 μm, 2 × 25 cm. 15% i-PrOH-hexane, 7.0 mL/min flow rate). The relative ratio of enatiomers was determined on an analytical Chiracel OD column (10 μm, 0.46 × 25 cm. 10% i-PrOH-hexane, 1.0 mL/min flow rate). The efluent was monitored at 235 nm, and the enantiomers eluted with a retention time of 9.98 (major S-23) and 11.48 min (minor R-23). respectively (α = 1.15).
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    • note
    • The epimers of 20 were chromatographically separated, and their relative ratio was determined on a semipreparative Diacel Chiracel OD column (10 μm, 2 × 25 cm, 50% i-PrOH-hexane. 7.0 mL/min flow rate). The effluent was monitored at 265 nm, and the diastereomers eluted with a retention time of 26.3 (20) and 32.3 min (epi-20), respectively (α = 1.23).
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    • Characterization of these three products may be found in the Supporting Information
    • Characterization of these three products may be found in the Supporting Information.
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    • 2O 3/1/1, 23 °C, 10 h (70%)
    • 2O 3/1/1, 23 °C, 10 h (70%).
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    • Altering the length of time exposed to the hydrolysis conditions alters the relative amounts of 1-3 obtained
    • Altering the length of time exposed to the hydrolysis conditions alters the relative amounts of 1-3 obtained.
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    • PCT Int. Appl. WO9401408
    • Dumaitre, B. A.: Dodic, N.; Daugan, A. C. M.; Pianetti, P. M. C. PCT Int. Appl. WO9401408; Chem. Abstr. 1995, 122, 31342e. A detailed procedure for the preparation of 33 is provided in the Supporting Information.
    • Dumaitre, B.A.1    Dodic, N.2    Daugan, A.C.M.3    Pianetti, P.M.C.4
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    • Dumaitre, B. A.: Dodic, N.; Daugan, A. C. M.; Pianetti, P. M. C. PCT Int. Appl. WO9401408; Chem. Abstr. 1995, 122, 31342e. A detailed procedure for the preparation of 33 is provided in the Supporting Information.
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    • Full characterization data are provided in the Supporting Information
    • Full characterization data are provided in the Supporting Information.


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