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Volumn , Issue 15, 2000, Pages 1341-1350

Synthetic studies on calicheamicin γ1(I)-synthesis of (-)-calicheamicinone and models representing the four sugars and the aromatic system

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CALICHEAMICIN DERIVATIVE; CALICHEAMICIN GAMMA1; CALICHEAMICINONE; CARBOHYDRATE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034617818     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001204l     Document Type: Article
Times cited : (33)

References (62)
  • 1
    • 0026045597 scopus 로고
    • Representative reviews on the chemistry and mode of action: K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 1991, 30, 1387; S. J. Danishefsky and M. D. Shair, J. Org. Chem., 1996, 61, 16; A. C. Weymeth-Wilson, Nat. Prod. Rep., 1997, 14, 99; J. A. Murphy and J. Griffiths, Nat. Prod. Rep., 1993, 10, 551.
    • (1991) Angew. Chem., Int. Ed. Engl. , vol.30 , pp. 1387
    • Nicolaou, K.C.1    Dai, W.-M.2
  • 2
    • 0030069884 scopus 로고    scopus 로고
    • Representative reviews on the chemistry and mode of action: K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 1991, 30, 1387; S. J. Danishefsky and M. D. Shair, J. Org. Chem., 1996, 61, 16; A. C. Weymeth-Wilson, Nat. Prod. Rep., 1997, 14, 99; J. A. Murphy and J. Griffiths, Nat. Prod. Rep., 1993, 10, 551.
    • (1996) J. Org. Chem. , vol.61 , pp. 16
    • Danishefsky, S.J.1    Shair, M.D.2
  • 3
    • 0031127564 scopus 로고    scopus 로고
    • Representative reviews on the chemistry and mode of action: K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 1991, 30, 1387; S. J. Danishefsky and M. D. Shair, J. Org. Chem., 1996, 61, 16; A. C. Weymeth-Wilson, Nat. Prod. Rep., 1997, 14, 99; J. A. Murphy and J. Griffiths, Nat. Prod. Rep., 1993, 10, 551.
    • (1997) Nat. Prod. Rep. , vol.14 , pp. 99
    • Weymeth-Wilson, A.C.1
  • 4
    • 0027714672 scopus 로고
    • Representative reviews on the chemistry and mode of action: K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int. Ed. Engl., 1991, 30, 1387; S. J. Danishefsky and M. D. Shair, J. Org. Chem., 1996, 61, 16; A. C. Weymeth-Wilson, Nat. Prod. Rep., 1997, 14, 99; J. A. Murphy and J. Griffiths, Nat. Prod. Rep., 1993, 10, 551.
    • (1993) Nat. Prod. Rep. , vol.10 , pp. 551
    • Murphy, J.A.1    Griffiths, J.2
  • 5
    • 0002125235 scopus 로고    scopus 로고
    • Reviews on synthesis: H. Lhermitte and D. S. Grierson, Contemp. Org. Synth., 1996, 3, 41; H. Lhermitte and D. S. Grierson, Contemp. Org. Synth., 1996, 3, 93.
    • (1996) Contemp. Org. Synth. , vol.3 , pp. 41
    • Lhermitte, H.1    Grierson, D.S.2
  • 6
    • 0002125234 scopus 로고    scopus 로고
    • Reviews on synthesis: H. Lhermitte and D. S. Grierson, Contemp. Org. Synth., 1996, 3, 41; H. Lhermitte and D. S. Grierson, Contemp. Org. Synth., 1996, 3, 93.
    • (1996) Contemp. Org. Synth. , vol.3 , pp. 93
    • Lhermitte, H.1    Grierson, D.S.2
  • 22
    • 0000016331 scopus 로고
    • Cf. S. Danishefsky, M. P. Prisbylla and S. Hiner, J. Am. Chem. Soc., 1978, 100, 2918; S. Danishefsky, Acc. Chem. Res., 1981, 14, 400.
    • (1981) Acc. Chem. Res. , vol.14 , pp. 400
    • Danishefsky, S.1
  • 25
    • 0343895171 scopus 로고    scopus 로고
    • note
    • 3 - 1:1.
  • 34
    • 0343459540 scopus 로고    scopus 로고
    • note
    • O-Methylation, DIBAL-H reduction of the ester to an aldehyde and acid-catalyzed desilylation and ring closure gave a pyranose with cis nitrogen and OMe groups, indicating that the hydroxy stereochemistry in 83 (major isomer) required inversion.
  • 38
    • 0343023829 scopus 로고    scopus 로고
    • ref. 21
    • (d) ref. 21;
  • 47
    • 0028309516 scopus 로고
    • (c) for synthesis based on Sharpless kinetic resolution, see: W. R. Roush and D. Gustin, Tetrahedron Lett., 1994, 35, 4931;
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4931
    • Roush, W.R.1    Gustin, D.2
  • 50
    • 84986665025 scopus 로고
    • ref. 21
    • For synthesis of a model from D-galactose, see: H. Rainer and H.-D. Scharf, Liebigs Ann. Chem., 1993, 117; ref. 21; for synthesis from crotonaldehyde, see: W. R. Roush and B. C. Follows, Tetrahedron Lett., 1994, 35, 4935; for synthesis from di-O-actyl-d-fucal, see ref. 24(f).
    • (1993) Liebigs Ann. Chem. , pp. 117
    • Rainer, H.1    Scharf, H.-D.2
  • 51
    • 0028365023 scopus 로고
    • for synthesis from di-O-actyl-d-fucal, see ref. 24(f)
    • For synthesis of a model from D-galactose, see: H. Rainer and H.-D. Scharf, Liebigs Ann. Chem., 1993, 117; ref. 21; for synthesis from crotonaldehyde, see: W. R. Roush and B. C. Follows, Tetrahedron Lett., 1994, 35, 4935; for synthesis from di-O-actyl-d-fucal, see ref. 24(f).
    • (1994) Tetrahedron Lett. , vol.35 , pp. 4935
    • Roush, W.R.1    Follows, B.C.2
  • 55
    • 0342589577 scopus 로고    scopus 로고
    • note
    • The route from 114 is similar to that reported by Danishefsky and coworkers [see ref. 24(f).
  • 57
    • 0343023822 scopus 로고    scopus 로고
    • note
    • For synthesis from D-rhamnose, see ref. 21(d); ref. 21; for synthesis from di-O-acetyl-L-rhamnal, see ref. 24(f).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.