A synthetic approach to benanomicin a: Synthesis of the substituted 5,6-dihydrobenzo[a]naphthacenequinone

Chemistry Letters

Volumn , Issue 4, 1997, Pages 305-306

  Hirosawa, Sehei ^a   Nishizuka, Toshio ^a   Kondo, Shinichi ^a   Ikeda, Daishiro ^a  

^a INSTITUTE OF MICROBIAL CHEMISTRY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031527247     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.305     Document Type: Article

References (16)

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7. For other syntheses of substituted 5,6-dihydrobenzo[a]-naphthacenequinones, see: F. M. Hauser and Y. Caringal, J. Org. Chem., 55, 555 (1990). T. R. Kelly, W. Xu, Z. Ma, Q. Li, and V. Bhushan, J. Am. Chem. Soc., 115, 5843 (1993). G. A. Kraus and G. Zhao, Synlett, 1995, 541. G. A. Kraus and G. Zhao, J. Org. Chem., 61, 2770 (1996).
8. For other syntheses of substituted 5,6-dihydrobenzo[a]-naphthacenequinones, see: F. M. Hauser and Y. Caringal, J. Org. Chem., 55, 555 (1990). T. R. Kelly, W. Xu, Z. Ma, Q. Li, and V. Bhushan, J. Am. Chem. Soc., 115, 5843 (1993). G. A. Kraus and G. Zhao, Synlett, 1995, 541. G. A. Kraus and G. Zhao, J. Org. Chem., 61, 2770 (1996).
9. For other syntheses of substituted 5,6-dihydrobenzo[a]-naphthacenequinones, see: F. M. Hauser and Y. Caringal, J. Org. Chem., 55, 555 (1990). T. R. Kelly, W. Xu, Z. Ma, Q. Li, and V. Bhushan, J. Am. Chem. Soc., 115, 5843 (1993). G. A. Kraus and G. Zhao, Synlett, 1995, 541. G. A. Kraus and G. Zhao, J. Org. Chem., 61, 2770 (1996).
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13. 5: C, 67.73; H, 6.50%.
14. 1H NMR integration of the olefin proton signals (δ 6.05 for Z-isomer and 7.03 for E).
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16. 3), 6.79 (1H, d, J=2.4 Hz, 10-H), 6.93 (1H, s, 4-H), 7.49 (1H, d, J=2.4 Hz, 12-H), 8.10 (1H, s, 7-H) and 9.15 (1H, s, 14-H).