Enantiotopical Synthesis of Carbazoquinocins a and D, the Potent Lipid Peroxidation Inhibitors from Streptomyces violaceus 2448-SVT2

Synlett

Volumn 1996, Issue 9, 1996, Pages 922-924

  Shin, Kogyoku ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002903238     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5618     Document Type: Article

References (29)

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3. Takano, S.; Sekiguchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1987, 555; Takano, S.; Sekiguchi, Y.; Sato, N.; Ogasawara, K. Synthesis 1987, 139.
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7. Takano, S.; Sekiguchi, Y.; Setoh, M.; Yoshimitsu, T.; Inomata, K.; Takahashi, M.; Ogasawara, K. Heterocycles 1990, 31, 1715; Reviews on the enantiocontrolled syntheses using chiral O-benzylglycidol, see: Takano, S.; Ogasawara, K. J. Syn. Org. Chem. Jpn. 1987, 45, 1157; 1989, 47, 813; Hanson, R. M. Chem. Rev. 1991, 91, 437.
8. Takano, S.; Sekiguchi, Y.; Setoh, M.; Yoshimitsu, T.; Inomata, K.; Takahashi, M.; Ogasawara, K. Heterocycles 1990, 31, 1715; Reviews on the enantiocontrolled syntheses using chiral O-benzylglycidol, see: Takano, S.; Ogasawara, K. J. Syn. Org. Chem. Jpn. 1987, 45, 1157; 1989, 47, 813; Hanson, R. M. Chem. Rev. 1991, 91, 437.
9. Takano, S.; Sekiguchi, Y.; Setoh, M.; Yoshimitsu, T.; Inomata, K.; Takahashi, M.; Ogasawara, K. Heterocycles 1990, 31, 1715; Reviews on the enantiocontrolled syntheses using chiral O-benzylglycidol, see: Takano, S.; Ogasawara, K. J. Syn. Org. Chem. Jpn. 1987, 45, 1157; 1989, 47, 813; Hanson, R. M. Chem. Rev. 1991, 91, 437.
10. 13C NMR, and MS) and analytical (combustion and/or high resolution MS) were obtained for all new compounds.
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22. This indole formation reaction has been proven to be particularly useful for the synthesis of the 2-substituted indole natural products: Takano, S.; Sato, T.; Inomata, K ; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1991, 402; Shin, K.; Ogasawara, K. Chem. Lett. 1995, 289; Shin, K.; Ogasawara, K. Synlett 1995, 859.
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29. 3) of the representative intermediates: (R)-13: δ=0.91 (d, 3H, J=6.2 Hz), 1.15-1.80 (m, 7H), 1.94 (t, 1H, J=2.6 Hz), 2.13 (td, 2H, J=6.6, 2.6 Hz), 2.80-3.07 (m, 2H), 7.08-7.40 (m, 5H). (R)-15: δ=0.90 (d, 3H, J=6.3 Hz), 1.06-1.74 (m, 11H), 1.94 (t, 1H, J=2.7 Hz), 2.18 (td, 2H, J=7.0, 2.7 Hz), 2.81-3.04 (m, 2H), 7.11-7.21 (m, 1H), 7.23-7.36 (m, 4H). 25a: δ=0.92 (t, 3H, J=7.3 Hz), 1.03 (d, 3H, J=6.0 Hz), 1.16-1.70 (m, 5H), 1.45 (t, 3H, J=7.1 Hz), 2.67 (s, 3H), 2.74-3.0 (m, 2H), 4.42 (q, 2H, J=7.1 Hz), 7.19-7.30 (m, 1H), 7.35-7.49 (m, 2H), 8.05 (d, 1H, J=7.7 Hz), 8.09 (br s, 1H), 8.49(s, 1H). 25b: δ=0.86 (t, 3H, J=7.1 Hz), 0.87 (d, 3H, J=6.3 Hz), 1.02-1.72 (m, 9H), 1.46 (t, 3H, J=7.1 Hz), 2.69 (s, 3H), 2.92 (t, 2H, J=8.0 Hz), 4.42 (q, 2H, J=7.1 Hz), 7.20-7.32 (m, 1H), 7.37-7.52 (m, 2H), 8.07 (d, 1H, J=8.0 Hz), 8.08 (br s, 1H), 8.50 (s, 1H).