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Volumn 74, Issue 15, 2009, Pages 5750-5753

An improved synthesis of pyridine-thiazole cores of thiopeptide antibiotics

Author keywords

[No Author keywords available]

Indexed keywords

THIOPEPTIDE ANTIBIOTICS;

EID: 68049109443     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900950x     Document Type: Article
Times cited : (46)

References (36)
  • 3
    • 68049099605 scopus 로고    scopus 로고
    • Major synthetic achievements. Promothiocin A: (a) Moody, C. J.; Bagley, M. C. Chem. Commun. 1998, 2049.
    • Major synthetic achievements. Promothiocin A: (a) Moody, C. J.; Bagley, M. C. Chem. Commun. 1998, 2049.
  • 5
    • 27644574520 scopus 로고    scopus 로고
    • Amythiamycin D: (c) Hughes, R. A.; Thompson, S. P.; Alcaraz, L.; Moody, C. J. J. Am. Chem. Soc. 2005, 127, 15644.
    • Amythiamycin D: (c) Hughes, R. A.; Thompson, S. P.; Alcaraz, L.; Moody, C. J. J. Am. Chem. Soc. 2005, 127, 15644.
  • 7
    • 23744471989 scopus 로고    scopus 로고
    • Thiostrepton: (e) Nicolaou, K. C.; Safina, B. S.; Zak, M.; Lee, S. H.; Nevalainen, M.; Bella, M.; Estrada, A. A.; Funke, C.; Zecri, F. J.; Bulat, S. J. Am. Chem. Soc. 2005, 127, 11159.
    • Thiostrepton: (e) Nicolaou, K. C.; Safina, B. S.; Zak, M.; Lee, S. H.; Nevalainen, M.; Bella, M.; Estrada, A. A.; Funke, C.; Zecri, F. J.; Bulat, S. J. Am. Chem. Soc. 2005, 127, 11159.
  • 11
    • 33846350838 scopus 로고    scopus 로고
    • Siomycin A: (i) Mori, T.; Higashibayashi, S.; Goto, T.; Kohno, M.; Satouchi, Y.; Shinko, K.; Suzuki, K.; Suzuki, S.; Tohmiya, H.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2007, 48, 1331.
    • Siomycin A: (i) Mori, T.; Higashibayashi, S.; Goto, T.; Kohno, M.; Satouchi, Y.; Shinko, K.; Suzuki, K.; Suzuki, S.; Tohmiya, H.; Hashimoto, K.; Nakata, M. Tetrahedron Lett. 2007, 48, 1331.
  • 12
    • 33845290273 scopus 로고    scopus 로고
    • GE2270A and GE 2270T: (j) Nicolaou, K. C, Zou, B, Dethe, D. H, Li, D. B, Chen, D. Y. K. Angew. Chem, Int. Ed. 2006, 45, 7786
    • GE2270A and GE 2270T: (j) Nicolaou, K. C.; Zou, B.; Dethe, D. H.; Li, D. B.; Chen, D. Y. K. Angew. Chem., Int. Ed. 2006, 45, 7786.
  • 15
    • 70349786238 scopus 로고    scopus 로고
    • Micrococcin P1: (m) Lefranc, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2009, 48, 4198.
    • Micrococcin P1: (m) Lefranc, D.; Ciufolini, M. A. Angew. Chem., Int. Ed. 2009, 48, 4198.
  • 17
    • 0036056973 scopus 로고    scopus 로고
    • Moody, C. J; Hughes, R. A.; Thompson, S. P.; Alcaraz, L. Chem. Commun. 2002, 1760. See also ref 2d.
    • (b) Moody, C. J; Hughes, R. A.; Thompson, S. P.; Alcaraz, L. Chem. Commun. 2002, 1760. See also ref 2d.
  • 18
    • 68049092397 scopus 로고    scopus 로고
    • Noteworthy in this regard is the Bach approach refs 2k and 2l, See ref 1 for a thorough bibliography
    • Noteworthy in this regard is the Bach approach (refs 2k and 2l). See ref 1 for a thorough bibliography.
  • 21
    • 35348959557 scopus 로고    scopus 로고
    • Moody introduced the reaction into current synthetic practice during his pioneering synthesis of promothiocin A (ref 2a, Review: b
    • Review: (b) Bagley, M. C.; Glover, C.; Merritt, E. A. Synlett 2007, 2459. Moody introduced the reaction into current synthetic practice during his pioneering synthesis of promothiocin A (ref 2a).
    • (2007) Synlett , pp. 2459
    • Bagley, M.C.1    Glover, C.2    Merritt, E.A.3
  • 24
    • 68049108737 scopus 로고    scopus 로고
    • For representative methods see the preparation of compounds 7 and 12 (Scheme 2 herein) as described in ref 5 (12, 8 steps from glycolonitrile, 25%), ref 8, and in the following: Merritt, E. A.; Bagley, M. C. Synlett 2007, 954 (7, 4 steps from diethoxyacetonitrile, 83%).
    • For representative methods see the preparation of compounds 7 and 12 (Scheme 2 herein) as described in ref 5 (12, 8 steps from glycolonitrile, 25%), ref 8, and in the following: Merritt, E. A.; Bagley, M. C. Synlett 2007, 954 (7, 4 steps from diethoxyacetonitrile, 83%).
  • 25
    • 68049098536 scopus 로고    scopus 로고
    • This reaction forms a black precipitate of Se byproducts. Perhaps this precipitate entrains byproducts arising from 11
    • This reaction forms a black precipitate of Se byproducts. Perhaps this precipitate entrains byproducts arising from 11.
  • 26
    • 68049103525 scopus 로고    scopus 로고
    • The use of IBX for the oxidation of such carbinols was introduced by Moody (refs 2a and 2b). We found that the Dess-Martin periodinane performed better than IBX in the oxidation of 15.
    • The use of IBX for the oxidation of such carbinols was introduced by Moody (refs 2a and 2b). We found that the Dess-Martin periodinane performed better than IBX in the oxidation of 15.
  • 27
    • 68049089132 scopus 로고    scopus 로고
    • This known compound was made as detailed in the Supporting Information
    • This known compound was made as detailed in the Supporting Information.
  • 31
    • 33644839140 scopus 로고    scopus 로고
    • A similar reaction may be carried out in ionic liquids: Karthikeyan, G.; Perumal, P. T. Can. J. Chem. 2005, 83, 1746.
    • A similar reaction may be carried out in ionic liquids: Karthikeyan, G.; Perumal, P. T. Can. J. Chem. 2005, 83, 1746.
  • 33
    • 0037300530 scopus 로고    scopus 로고
    • YM-266183: Nagai, K, Kamigiri, K, Arao, N, Suzumura, K.-I, Kawano, Y, Yamaoka, M, Zhang, H, Watanabe, M, Suzuki, K. J. Antibiot. 2003, 56, 123
    • YM-266183: Nagai, K.; Kamigiri, K.; Arao, N.; Suzumura, K.-I.; Kawano, Y.; Yamaoka, M.; Zhang, H.; Watanabe, M.; Suzuki, K. J. Antibiot. 2003, 56, 123.
  • 34
    • 68049112861 scopus 로고    scopus 로고
    • Conduct of the reaction in EtOH again failed to produce pyridines
    • Conduct of the reaction in EtOH again failed to produce pyridines.
  • 35
    • 68049104581 scopus 로고    scopus 로고
    • Experimental protocols are provided as Supporting Information
    • Experimental protocols are provided as Supporting Information.
  • 36
    • 68049093425 scopus 로고    scopus 로고
    • Details of the HPLC analysis are provided as Supporting Information
    • Details of the HPLC analysis are provided as Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.