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Volumn , Issue 1, 2004, Pages 131-133

Regio- and Stereoselective Synthesis of α-Chiral 2-Substituted 4-Bromothiazoles from 2,4-Dibromothiazole by Bromine-Magnesium Exchange. Building Blocks for the Synthesis of Thiazolyl Peptides and Dolabellin

Author keywords

Asymmetric synthesis; Magnesium; Metalations; Natural products; Thiazoles

Indexed keywords

BROMINE; MAGNESIUM; THIAZOLE DERIVATIVE;

EID: 0348231749     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-43361     Document Type: Article
Times cited : (30)

References (40)
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    • Selected examples: (a) Buchanan, J. L.; Bohacek, R. S.; Luke, G. P.; Hatada, M.; Lu, X.; Dalgarno, D. C.; Narula, S. S.; Yuan, R.; Holt, D. A. Bioorg. Med. Chem. Lett. 1999, 9, 2353. (b) Bagley, M. C.; Bashford, K. E.; Hesketh, C. L.; Moody, C. J. J. Am. Chem. Soc. 2000, 122, 3301. (c) Xia, Z.; Smith, C. D. J. Org. Chem. 2001, 66, 3459. (d) Lee, C. B.; Wu, Z.; Zhang, F.; Chappell, M. D.; Stachel, S. J.; Chou, T.-C.; Guan, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 5249. (e) Cetusic, J. R. P.; Green, F. R. III; Graupner, P. R.; Oliver, M. P. Org. Lett. 2002, 4, 1307.
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    • Lee, C.B.1    Wu, Z.2    Zhang, F.3    Chappell, M.D.4    Stachel, S.J.5    Chou, T.-C.6    Guan, Y.7    Danishefsky, S.J.8
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    • Selected examples: (a) Wipf, P.; Venkatraman, S. J. Org. Chem. 1996, 61, 8004. (b) Heck, S.; Dömling, A. Synlett 2000, 424. (c) Boden, C. D. J.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 2000, 875. (d) Frontrodona, X.; Diaz, S.; Linden, A.; Villalgordo, J. M. Synthesis 2001, 2021. (e) Sugiyama, H. ; Yokokawa, F.; Shioiri, T. Tetrahedron 2003, 59, 6579.
    • (2000) Synlett , pp. 424
    • Heck, S.1    Dömling, A.2
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    • 0034696496 scopus 로고    scopus 로고
    • Selected examples: (a) Wipf, P.; Venkatraman, S. J. Org. Chem. 1996, 61, 8004. (b) Heck, S.; Dömling, A. Synlett 2000, 424. (c) Boden, C. D. J.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 2000, 875. (d) Frontrodona, X.; Diaz, S.; Linden, A.; Villalgordo, J. M. Synthesis 2001, 2021. (e) Sugiyama, H. ; Yokokawa, F.; Shioiri, T. Tetrahedron 2003, 59, 6579.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 875
    • Boden, C.D.J.1    Pattenden, G.2
  • 13
    • 0034792964 scopus 로고    scopus 로고
    • Selected examples: (a) Wipf, P.; Venkatraman, S. J. Org. Chem. 1996, 61, 8004. (b) Heck, S.; Dömling, A. Synlett 2000, 424. (c) Boden, C. D. J.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 2000, 875. (d) Frontrodona, X.; Diaz, S.; Linden, A.; Villalgordo, J. M. Synthesis 2001, 2021. (e) Sugiyama, H. ; Yokokawa, F.; Shioiri, T. Tetrahedron 2003, 59, 6579.
    • (2001) Synthesis , pp. 2021
    • Frontrodona, X.1    Diaz, S.2    Linden, A.3    Villalgordo, J.M.4
  • 14
    • 0043204444 scopus 로고    scopus 로고
    • Selected examples: (a) Wipf, P.; Venkatraman, S. J. Org. Chem. 1996, 61, 8004. (b) Heck, S.; Dömling, A. Synlett 2000, 424. (c) Boden, C. D. J.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 2000, 875. (d) Frontrodona, X.; Diaz, S.; Linden, A.; Villalgordo, J. M. Synthesis 2001, 2021. (e) Sugiyama, H. ; Yokokawa, F.; Shioiri, T. Tetrahedron 2003, 59, 6579.
    • (2003) Tetrahedron , vol.59 , pp. 6579
    • Sugiyama, H.1    Yokokawa, F.2    Shioiri, T.3
  • 21
    • 23544447476 scopus 로고    scopus 로고
    • PhD Thesis; Technical University: Munich
    • Spieß, A. PhD Thesis; Technical University: Munich, 2003.
    • (2003)
    • Spieß, A.1
  • 35
    • 0346164266 scopus 로고    scopus 로고
    • note
    • 2OSSi (413.45): C, 49.39; H, 6.09; N, 6.78. Found: C, 49.45; H, 6.11; N, 6.71. The erythrodiastereoisomer (0.47g, 1. 13 mmol, 11%) was obtained as a yellow liquid.
  • 36
    • 0346164268 scopus 로고    scopus 로고
    • note
    • 2O/MeCN 20:80→0: 100 over 30 min; flow rate: 1.0 mL/ min).
  • 39
    • 0346794806 scopus 로고    scopus 로고
    • note
    • 10BrNOS (236.13): C, 35.61; H, 4.27; N, 5.93. Found: C, 35.81; H, 4.38; N, 5.87.
  • 40
    • 0346794804 scopus 로고    scopus 로고
    • note
    • 3S (215.27): C, 50.21; H, 6.09; N, 6.51. Found: C, 49.91; H, 6.20; N, 6.29.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.