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Volumn 68, Issue 5, 2003, Pages 2006-2009

Stereoselective synthesis of 1′-C-branched arabinofuranosyl nucleosides via anomeric radicals generated by 1,2-acyloxy migration

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERIC RADICALS;

EID: 0037424423     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo020620d     Document Type: Article
Times cited : (12)

References (24)
  • 7
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    • ′-C-Acylated derivatives of 2′-deoxyuridine were synthesized as anomeric radical precursors. (a) Greenberg, M. M.; Yoo, D. J.; Goodman, B. K. Nucleosides Nucleotides 1997, 16, 33-40. (b) Chatgilialoglu, C.; Gimisis, T. Chem. Commun. 1998, 1249-1250. (c) Chatgilialoglu, C.; Ferreri, C.; Gimisis, T. Tetrahedron Lett. 1999, 40, 2837-2840.
    • (1997) Nucleosides Nucleotides , vol.16 , pp. 33-40
    • Greenberg, M.M.1    Yoo, D.J.2    Goodman, B.K.3
  • 8
    • 0001794825 scopus 로고    scopus 로고
    • ′-C-Acylated derivatives of 2′-deoxyuridine were synthesized as anomeric radical precursors. (a) Greenberg, M. M.; Yoo, D. J.; Goodman, B. K. Nucleosides Nucleotides 1997, 16, 33-40. (b) Chatgilialoglu, C.; Gimisis, T. Chem. Commun. 1998, 1249-1250. (c) Chatgilialoglu, C.; Ferreri, C.; Gimisis, T. Tetrahedron Lett. 1999, 40, 2837-2840.
    • (1998) Chem. Commun. , pp. 1249-1250
    • Chatgilialoglu, C.1    Gimisis, T.2
  • 9
    • 0033515728 scopus 로고    scopus 로고
    • ′-C-Acylated derivatives of 2′-deoxyuridine were synthesized as anomeric radical precursors. (a) Greenberg, M. M.; Yoo, D. J.; Goodman, B. K. Nucleosides Nucleotides 1997, 16, 33-40. (b) Chatgilialoglu, C.; Gimisis, T. Chem. Commun. 1998, 1249-1250. (c) Chatgilialoglu, C.; Ferreri, C.; Gimisis, T. Tetrahedron Lett. 1999, 40, 2837-2840.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2837-2840
    • Chatgilialoglu, C.1    Ferreri, C.2    Gimisis, T.3
  • 12
    • 0029123966 scopus 로고
    • Kinetic studies of the 1,2-acyloxy migaration have been reported: (a) Gimisis, T.; Ialongo, G.; Zamboni, M.; Chatgilialoglu, C. Tetrahedron Lett. 1995, 36, 6781-6784. Chatgilialoglu, C. Tetrahedron Lett. 1995, 36, 6781-6784. (b) Gimisis, T.; Ialongo; Chatgilialoglu, C. Tetrahedron 1998, 54, 573-592. (c) Chatogilialoglu, C. Nucleosides Nucleotides 1999, 18, 547-553.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 6781-6784
    • Gimisis, T.1    Ialongo, G.2    Zamboni, M.3    Chatgilialoglu, C.4
  • 13
    • 0032518804 scopus 로고    scopus 로고
    • Kinetic studies of the 1,2-acyloxy migaration have been reported: (a) Gimisis, T.; Ialongo, G.; Zamboni, M.; Chatgilialoglu, C. Tetrahedron Lett. 1995, 36, 6781-6784. (b) Gimisis, T.; Ialongo; Chatgilialoglu, C. Tetrahedron 1998, 54, 573-592. (c) Chatogilialoglu, C. Nucleosides Nucleotides 1999, 18, 547-553.
    • (1998) Tetrahedron , vol.54 , pp. 573-592
    • Gimisis, T.1    Ialongo2    Chatgilialoglu, C.3
  • 14
    • 0033021789 scopus 로고    scopus 로고
    • Kinetic studies of the 1,2-acyloxy migaration have been reported: (a) Gimisis, T.; Ialongo, G.; Zamboni, M.; Chatgilialoglu, C. Tetrahedron Lett. 1995, 36, 6781-6784. (b) Gimisis, T.; Ialongo; Chatgilialoglu, C. Tetrahedron 1998, 54, 573-592. (c) Chatogilialoglu, C. Nucleosides Nucleotides 1999, 18, 547-553.
    • (1999) Nucleosides Nucleotides , vol.18 , pp. 547-553
    • Chatogilialoglu, C.1
  • 15
    • 0035354786 scopus 로고    scopus 로고
    • Recently, intra- and intermolecular C-C bond formation of nucleoside-1-yl has been reported: (a) (Intramolecular reaction) Kodama, T.; Shuto, S.; Nomura, M.; Matsuda, A. Chem. Eur. J. 2001, 7, 2332-2340. (b) (Intermolecular reaction) Kumamoto, H.; Murasaki, M.; Haraguchi, K.; Anamura, A.; Tanaka, H. J. Org. Chem. 2002, 67, 6124-6130.
    • (2001) Chem. Eur. J. , vol.7 , pp. 2332-2340
    • Kodama, T.1    Shuto, S.2    Nomura, M.3    Matsuda, A.4
  • 16
    • 0037162663 scopus 로고    scopus 로고
    • Recently, intra- and intermolecular C-C bond formation of nucleoside-1-yl has been reported: (a) (Intramolecular reaction) Kodama, T.; Shuto, S.; Nomura, M.; Matsuda, A. Chem. Eur. J. 2001, 7, 2332-2340. (b) (Intermolecular reaction) Kumamoto, H.; Murasaki, M.; Haraguchi, K.; Anamura, A.; Tanaka, H. J. Org. Chem. 2002, 67, 6124-6130.
    • (2002) J. Org. Chem. , vol.67 , pp. 6124-6130
    • Kumamoto, H.1    Murasaki, M.2    Haraguchi, K.3    Anamura, A.4    Tanaka, H.5
  • 20
    • 0242497139 scopus 로고    scopus 로고
    • note
    • The stereochemistry of these adducts was determined on the basis of NOE experiments: 12, H-2′/H-3′ and H-4′/H-8; 13, H-2′/H-4′.
  • 22
    • 0242413895 scopus 로고    scopus 로고
    • note
    • The stereochemistry of 14 was confirmed on the basis of the observation of NOEs between H-3′/H-6 and H-2′/H-4′.
  • 23
    • 0242497138 scopus 로고    scopus 로고
    • note
    • Although styryl(tributyl)stannane and 3-bromo-2-methylacrylonitrile used were a mixture of geometric isomers, the respective products 16 and 17 appeared to consist of only the depicted isomer. The configurations about the 1′- and 2′-positions of these products were confirmed on the basis of the observation of NOE correlations between H-3′ and H-6 and H-2′ and H-4′, respectively.
  • 24
    • 0000155866 scopus 로고    scopus 로고
    • Stereoselectivity of radical reactions: Cyclic systems
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • Renaud, P. Stereoselectivity of Radical Reactions: Cyclic Systems. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 400-415.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 400-415
    • Renaud, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.