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Volumn 129, Issue 50, 2007, Pages 15460-15461

An efficient synthetic approach to cyanocycline A and bioxalomycin β2 via [C+NC+CC] coupling

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BIOXALOMYCIN BETA2; CYANOCYCLINE A; NATURAL PRODUCT; PALLADIUM; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 37849035988     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077853c     Document Type: Article
Times cited : (36)

References (25)
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    • 1-catalyzed endo selective [C+NC+CC] coupling: Garner, P.; Kaniskan, H. Ü.; Hu, J.; Youngs, W. J.; Panzner, M. Org. Lett. 2006, 8, 3647.
    • 1-catalyzed endo selective [C+NC+CC] coupling: Garner, P.; Kaniskan, H. Ü.; Hu, J.; Youngs, W. J.; Panzner, M. Org. Lett. 2006, 8, 3647.
  • 2
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    • 1-catalyzed exo selective [C+NC+CC] coupling: Garner, P.; Hu, J.; Parker, C. G.; Youngs, W. J.; Medvetz, D. Tetrahedron Lett. 2007, 48, 3867.
    • 1-catalyzed exo selective [C+NC+CC] coupling: Garner, P.; Hu, J.; Parker, C. G.; Youngs, W. J.; Medvetz, D. Tetrahedron Lett. 2007, 48, 3867.
  • 3
    • 0027939969 scopus 로고    scopus 로고
    • Zaccardi, J.; Alluri, M.; Ashcroft, J.; Bernan, V.; Korshalla, J. D.; Morton, G. O.; Siegel, M.; Tsao, R.; Williams, D. R.; Maiese, W.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4045. This paper established that the originally proposed structure of naphthyridinomycin was likely the G-ring hydrolysate and that the natural product is, in fact, bioxalomycin β2.
    • Zaccardi, J.; Alluri, M.; Ashcroft, J.; Bernan, V.; Korshalla, J. D.; Morton, G. O.; Siegel, M.; Tsao, R.; Williams, D. R.; Maiese, W.; Ellestad, G. A. J. Org. Chem. 1994, 59, 4045. This paper established that the originally proposed structure of naphthyridinomycin was likely the G-ring hydrolysate and that the natural product is, in fact, bioxalomycin β2.
  • 4
    • 0036558479 scopus 로고    scopus 로고
    • For, a comprehensive review of the chemistry and biology of the saframycin, quinocarcin, and naphthyridinomycin families of tetrahydroisoquinoline antibiotics, see
    • For, a comprehensive review of the chemistry and biology of the saframycin, quinocarcin, and naphthyridinomycin families of tetrahydroisoquinoline antibiotics, see: Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669.
    • (2002) Chem. Rev , vol.102 , pp. 1669
    • Scott, J.D.1    Williams, R.M.2
  • 5
    • 0028063505 scopus 로고    scopus 로고
    • While the tetrahydroisoquinoline antibiotics were originally believed to act as DNA-damaging, cytotoxins, there is increasing evidence that these molecules also interact with therapeutically relevant proteins: (a) dnacin inhibits dual specificity phosphatase cdc25B: Horiguchi, T, Nishi, K, Hakoda, S, Tanida, S, Nagata, A, Okayama, H. Biochem. Pharmacol. 1994, 48, 2139
    • While the tetrahydroisoquinoline antibiotics were originally believed to act as DNA-damaging, cytotoxins, there is increasing evidence that these molecules also interact with therapeutically relevant proteins: (a) dnacin inhibits dual specificity phosphatase cdc25B: Horiguchi, T.; Nishi, K.; Hakoda, S.; Tanida, S.; Nagata, A.; Okayama, H. Biochem. Pharmacol. 1994, 48, 2139.
  • 6
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    • DX-52-1 inhibits radixin: Kahsai, A. W, Zhu, S, Wardrop, D. J, Lane, W. S, Fenteany, G. Chem. Biol. 2006, 13, 973
    • (b) DX-52-1 inhibits radixin: Kahsai, A. W.; Zhu, S.; Wardrop, D. J.; Lane, W. S.; Fenteany, G. Chem. Biol. 2006, 13, 973.
  • 7
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    • ET-743 inhibits DNA repair proteins: D'Incalci, M, Erba, E, Damia, G, Gallera, E, Carrassa, L, Marchini, S, Mantovani, R, Tognon, G, Fruscio, R, Jimeno, J, Faircloth, G. T. The Oncologist 2002, 7, 210
    • (c) ET-743 inhibits DNA repair proteins: D'Incalci, M.; Erba, E.; Damia, G.; Gallera, E.; Carrassa, L.; Marchini, S.; Mantovani, R.; Tognon, G.; Fruscio, R.; Jimeno, J.; Faircloth, G. T. The Oncologist 2002, 7, 210.
  • 8
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    • Synthesis of rac-cyanocycline A: (a) Evans, D. A.; Illig, C. A.; Saddler, J. C. J. Am. Chem. Soc. 1986, 108, 2478.
    • Synthesis of rac-cyanocycline A: (a) Evans, D. A.; Illig, C. A.; Saddler, J. C. J. Am. Chem. Soc. 1986, 108, 2478.
  • 10
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    • Illig, C. R. Ph.D. Dissertation, Harvard University, Cambridge, MA, 1987.
    • (c) Illig, C. R. Ph.D. Dissertation, Harvard University, Cambridge, MA, 1987.
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  • 12
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    • Synthesis of (+)-naphthyridinomycin: Fukuyama, T
    • (e) Synthesis of (+)-naphthyridinomycin: Fukuyama, T. Adv. Heterocycl. Chem. 1992, 2, 189.
    • (1992) Adv. Heterocycl. Chem , vol.2 , pp. 189
  • 13
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    • Other synthetic efforts: (f) Danishefsky, S.; O'Neill, B. T.; Taniyama, E.; Vaughn, K. Tetrahedron Lett. 1984, 25, 4199.
    • Other synthetic efforts: (f) Danishefsky, S.; O'Neill, B. T.; Taniyama, E.; Vaughn, K. Tetrahedron Lett. 1984, 25, 4199.
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  • 19
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    • The bromide corresponding to 1 was prepared by benzylation of the known 5-bromo-2,4-dimetnoxy-3-methylphenol: Marques, M. M.; Pichlmair, M. M. B.; Martin, H. J.; Mulzer, J. Synthesis 2002, 2766.
    • The bromide corresponding to 1 was prepared by benzylation of the known 5-bromo-2,4-dimetnoxy-3-methylphenol: Marques, M. M.; Pichlmair, M. M. B.; Martin, H. J.; Mulzer, J. Synthesis 2002, 2766.
  • 21
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    • This compound was conveniently prepared by acylation of Oppolzer's L-camphorsultam with bromoacetyl bromide followed by displacement by azide and hydrogenolysis. See: Kaniskan, H. Ü. Ph.D. Dissertation, Case Western Reserve University, Cleveland, OH, 2007
    • This compound was conveniently prepared by acylation of Oppolzer's L-camphorsultam with bromoacetyl bromide followed by displacement by azide and hydrogenolysis. See: Kaniskan, H. Ü. Ph.D. Dissertation, Case Western Reserve University, Cleveland, OH, 2007.
  • 25
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    • Compound 12 has been found to inhibit cell migration, like DX-52-1, and has target overlap with DX-52-1 but has far greater selectivity for one target over another: Fenteany, G. Personal communication. This finding supports our hypothesis that this natural product family, now readily accessible using the strategy disclosed herein, will be useful for protein interrogation and drug development
    • Compound 12 has been found to inhibit cell migration, like DX-52-1, and has target overlap with DX-52-1 but has far greater selectivity for one target over another: Fenteany, G. Personal communication. This finding supports our hypothesis that this natural product family - now readily accessible using the strategy disclosed herein - will be useful for protein interrogation and drug development.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.