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Volumn 63, Issue 24, 2007, Pages 5189-5199

Total synthesis of (±)-methyl-kinamycin C

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3,4,4A PENTAHYDROXY 6,7,11 TRIMETHOXY 3 METHYL 1,2,3,4,4A,11B HEXAHYDROXYBENZO[B]FLUOREN 5 ONE; 1,3,4,4A TETRAHYDROXY 6,7,11 TRIMETHOXY 3 METHYL 3,4,4A,11B TETRAHYDRO 1H BENZO[B]FLUORENE 2,5 DIONE; 1,4A DIHYDROXY 6,7,11 TRIMETHOXY 3 METHYL 4A,11B DIHYDRO 1H BENZO[B]FLUORENE 5 DIONE; 2 HYDROXY 3 METHYL 1,3,4,4A TETRAKIS(TRIMETHYLSILANYLOXY) 6,7 11 TRIMETHOXY 1,2,3,4,4A,11B HEXAHYDROBENZO[B]FLUOREN 11 ONE; 2,4 DIACETOXY 3 HYDROXY 6,7,11 TRIMETHOXY 3 METHYL 5 (4 TOLUENESULFONYLHYDRAZONO) 2,3,4,5 TETRAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETIC ACID; 2,4 DIACETOXY 3 HYDROXY 6,7,11 TRIMETHOXY 3 METHYL 5 OXO 2,3,4,5 TETRAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETIC ACID; 2,4 DIACETOXY 3,4 DIHYDROXY 6,7,11 TRIMETHOXY 3 METHYL 5 OXO 2,3,4,4A,5,11B HEXAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETATE; 2,4 DIACETOXY 3,4A BIS(METHYLSULFANYLTHIOCARBOXYOXY) 6,7,11 TRIMETHOXY 3 METHYL 5 OXO 2,3,4,4A,5,11B HEXAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETATE; 2,4 DIACETOXY 6,7,11 TRIMETHOXY 3 METHYL 3 METHYLSULFANYL 5 OXO 2,3,4,5,TETRAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETATE; 2,4 DIACETOXY 6,7,11 TRIMETHOXY 3 METHYL 5 OXO 1 SULFAMYLOXY 2,3,4,11,TETRAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETATE; 3 METHYL 6,7,11 TRIMETHOXY 1,2,3,4,4A,11B HEXAHYDROXYBENZO[B]FLUORENE 1,2,3,4,4A,11B HEXAOL; 3,4,4A TRIHYDROXY 6,7,11 TRIMETHOXY 3 METHYL 3,4,4A,11B TETRAHYDRO 1H BENZO[B]FLUORENE 2,5 DIONE; 3,4A DIHYDROXY 6,7,11 TRIMETHOXY 3 METHYL 2,5 DIOXO 3,4,4A,11B TETRAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETATE; 4 ACETOXY 2,3 (DIMETHYLMETHYLENEDIOXY) 6,7,11 TRIMETHOXY 3 METHYL 5 OXO 2,3,4,4A,5 TETRAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETIC ACID; 4 ACETOXY 2,3 DIMETHYLMETHYLENEDIOXY 4A HYDROXY 6,7,11 TRIMETHOXY 3 METHYL 5 OXO 2,3,4,4A,5,11B HEXAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETIC ACID; 4 ACETOXY 2,3,4A TRIHYDROXY 6,7,11 TRIMETHOXY 3 METHYL 5 OXO 2,3,4,4A,5,11B HEXAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETIC ACID; 4 ACETOXY 3,4A DIHYDROXY 6,7,11 TRIMETHOXY 3 METHYL 2,5 DIOXO 2,3,4,4A,5,11B HEXAHYDRO 1H BENZO[B]FLUOREN 1 YL ACETIC ACID; 6,7,11 TRIMETHOXY 3 METHYL 1,2,5,11B TETRAHYDROXYBENZO[B]FLUORENE 1,2,4A,5 TETRAOL; 6,7,11 TRIMETHOXY 3 METHYL 1,3,4,4A TETRAKIS(TRIMETHYLSILANYLOXY) 3,4,4A,11B TETRAHYDRO 1H BENZO[B]FLUORENE 2,5 DIONE; 6,7,11 TRIMETHOXY 3 METHYL 1,4A BIS(TRIMETHYLSILANYLOXY) 4A,11B DIHYDROXYBENZO[B]FLUORENE 5 ONE; 6,7,11 TRIMETHOXY 3 METHYL 2,3,4,4A TETRAKIS(TRIMETHYLSILANYLOXY) 3,4,4A,11B TETRAHYDROXYBENZO[B]FLUOREN 5 ONE; ALKADIENE; BENZINDENONE; KINAMYCIN; METHYL KINAMYCIN C; UNCLASSIFIED DRUG;

EID: 34248183653     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.166     Document Type: Article
Times cited : (38)

References (43)
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    • For reviews, see:
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    • note
    • -1. See: Ref. 4.
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    • The terms prekinamycin and isoprekinamycin are now applied to the structures 4 and 5, respectively, because Gould reported the isolation of 4 as another metabolite produced by S. murayamaensis ( )
    • The terms prekinamycin and isoprekinamycin are now applied to the structures 4 and 5, respectively, because Gould reported the isolation of 4 as another metabolite produced by S. murayamaensis (. Gould S.J., Chen J., Cone M.C., Gore M.P., Melville C.R., and Tamayo N. J. Org. Chem. 61 (1996) 5720-5721 )
    • (1996) J. Org. Chem. , vol.61 , pp. 5720-5721
    • Gould, S.J.1    Chen, J.2    Cone, M.C.3    Gore, M.P.4    Melville, C.R.5    Tamayo, N.6
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    • note
    • The structure of 14 was deduced by comparison of spectral data with that of by-product obtained in model system (Kumamoto, T.; Ishikawa, T. Unpublished result). The detail will be reported elsewhere.
  • 29
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    • * in Figure 3 were observed, but the intensities were observed over 50% for several times.
  • 30
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    • Modified procedure of Hurst et al.
    • Modified procedure of Hurst et al. Hurst D.T., and McInnes A.G. Can. J. Chem. 43 (1965) 2004-2011
    • (1965) Can. J. Chem. , vol.43 , pp. 2004-2011
    • Hurst, D.T.1    McInnes, A.G.2
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    • note
    • 2)=0.0999. CCDC 638781.
  • 34
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    • note
    • 2)=0.1362. CCDC 618952.
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    • Displacement of benzylic xanthate to methylthio group in thermal condition was reported:
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    • 3 via five-membered ring transition state for the synthesis of rocaglaols:
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    • note
    • Ketal formation in 4-cyclohexene-trans-1,2-diol system has already been reported in the derivatization of kinamycins: see, Ref. 4b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.