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Volumn 16, Issue 23, 2005, Pages 3865-3876

An efficient approach to enantiomeric isoxazolidinyl analogues of tiazofurin based on nitrone cycloadditions

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLONITRILE; CARBON; CYSTEINE; ISOXAZOLIDINE DERIVATIVE; NITROGEN; NITRONE DERIVATIVE; THIAZOLE DERIVATIVE; TIAZOFURIN;

EID: 28644450748     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.11.004     Document Type: Article
Times cited : (48)

References (54)
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    • (Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; and Pople, J. A.; Gaussian, Pittsburgh PA, 2003).
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    • Interestingly, the (5S)-configuration of the major adducts is opposite to that found by Vasella (see Ref. 16) for the cycloaddition between N-ribosyl-C-(alkoxymethyl) nitrones and methyl methacrylate, thus pointing out the influence in the diastereofacial selectivity of the reaction not only of the chiral auxiliary but also of the dipolarophile's nature.
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    • Attempts of deprotecting the N-benzyl group included hydrogenation under mild conditions and reduction with Na and Li in liquid ammonia. A less common method, such as Montmorillonite K-10, which had successfully been used by us with other N-benzyl isoxazolidinyl nucleosides (see Ref. 8c) was also tested. In all cases complex reaction mixtures were obtained.
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    • Furthermore, the use of different N-glycosyl units, such as mannosyl, gulosyl, or erythrosyl derivatives, which are available in both enantiomeric forms, could provide access to both enantiomeric series. For representative examples of the use of those nitrones, see: K. Kasahara, H. Iida, and C. Kibayashi J. Org. Chem. 54 1989 2225 2233
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    • Kasahara, K.1    Iida, H.2    Kibayashi, C.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.