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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 20, 1990 - Issue 10
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Original Articles

A New Approach to the Synthetic Intermediates of Anthracyclinones Via Sequential C2-Symmetrical Naphthalene Derivatives

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Pages 1569-1575 | Received 13 Mar 1990, Published online: 24 Oct 2006

References

  • Arcamone , F. 1977 . Lloydia , 40 : 45 Idem, in, Topics in Antibiotic Chemistry, Vol. 2, ed. by Sammes, P. G., Horwood, E., Chichester, England, 1979; pp. 99. Oki, T., Takeuchi, T. Yuki Gosei Kagaku Kyokai Shi, 1982, 40, 2. See also: Ishizumi, K., Ohashi, N., Tanno, N. J. Org. Chem., 1987, 52, 4477, and references cited therein
  • Terashima , S. 1982 . Yuki Gosei Kagaku Kyokai Shi , 40 : 20 Tamura, Y., Sasho, M., Arai, S., Wada, A., Kita, Y. Tetrahedron, 1984, 40(22), 4539, and all other papers appearing in the same issue. Krohn, K. Angew. Chem., Int. Ed. Engl., 1986, 25, 790
  • Takahashi , I. and Terashima , S. 1982 . Chem. Pharm. Bull. , 30 : 4539 Previously, we found that the 2-substituted 1,8-dioxygenated-9(or 10)-hydroxyanthracenes could easily be subjected to the aerial oxidation to give the corresponding anthraquinones, the reaction analogous to that from 3 to 2. See also
  • Gleim , R. D. , Trenbeath , S. , Suzuki , F. and Sih , C. J. 1978 . J. Chem. Soc., Chem. Commun. , : 242 Sih, C. J.; Massuda, D.; Corey, P.; Gleim, R. D.; Suzuki, F. Tetrahedron Lett., 1979, 1285, Kende, A. S.; Johnson, S. J. Org. Chem., 1985, 50, 727.
  • Parker , K. A. and Kallmerten , J. L. 1979 . Tetrahedron Lett. , : 1197
  • Miersch , W. 1892 . Ber. , 25 : 2109 Hey, D. H., Nagdy, K. A. J. Chem. Soc., 1953, 1894. Uhlig, F. Angew. Chem., 1954, 66, 435
  • Kende , A. S. and Curran , D. P. 1978 . Tetrahedron Lett. , : 3003 Idem, J. Am. Chem. Soc., 1979, 101, 1857 For the examples along this line in total syntheses:
  • All new compounds were characterized by IR, 1H-NMR (270 MHz) and MASS or combustion analysis. Melting points are uncorrected. Chemical yields are those of pure (from TLC and NMR) samples obtained from chromatographic purifications
  • Adams , R. and Thal , A. F. 1932 . Organic Syntheses, Coll. , Edited by: Gilman , H. and Blatt , A. H. Vol. I , 270 New York : John Wiley &; Sons, Inc. .
  • Treatment of 10 under Hoesch reaction condition resulted in a complete recovery of the starting material. As for the investigations using 12, double annulation by use of other reagents (conc. H2SO4, FSO3, H (CF3CO)2O, ZnCl2 for acid 12; AlCl3, TiCl4, ZnCl2, BF3 Et2O for acid chloride of 12, etc.) did not give any satisfactory results; from spectral studies on the crude products, intermolecular, substitution to para, (peri) position was assumed. Reaction of 12 with PPA gave the desired 12 but in 34% yield
  • Kende , A. S. , Belletire , J. L. and Hume , E. 1974 . Tetrahedron Lett. , : 2117 See also: Gilmore, R. C., Jr. J. Am. Chem. Soc., 1951, 73, 5879
  • Data for tetracyclic diketone 4; mp 259–260° (decomp.); 1H-NMR (CDCl3., 270 MHz): δppm = 8.64 (2H, s), 3.95 (6H, s), 3.14 (4H, t, J, = 6.1 Hz), 2.76 (4H, t, J, = 6.6 Hz), 2.18 (4H, tt, J, = 6.1 Hz & 6.6 Hz); IR (CHBr3): vmax = 1682 cm−1 (C=0)
  • Djerassi , C. and Scholtz , C. R. 1948 . J. Am. Chem. Soc. , 70 : 417
  • Formation of α-mono-bromotetralone structure was confirmed basing upon the spectral data of dibromide A, which was prepared in quantitative yield from the reaction of 4 with 2.2 molar equiv. of Py.HBr.Br2. Data for dibromide A; mp 199–200° (decomp.); 1H-NMR (CDCl3, 270 MHz): δppm = 8.74 (2H, s), 4.84 (2H, dd, J, = J' = 4.4 Hz), 4.00 (6H, s), 3.30 (4H, broad t, J, = 6.4 Hz), 2.56 (4H, m); IR (CHBr3): vmax = 1687 cm−1 (C = 0)
  • Holysz , R. P. 1953 . J. Am. Chem. Soc. , 75 : 4432
  • Recovery of 4 at this stage was assumed as the result of a competitive side reaction (de-methylbromination), not as a simple “recovery” of the starting material
  • Bowden , K. , Heilbron , I. M. , Jones , E. R. H. and Weedon , B. C. L. 1946 . J. Chem. Soc. , : 39
  • Boeckman , R. K. Jr. , Delton , M. H. , Dolak , T. M. , Watanabe , T. and Glick , M. D. 1979 . J. Org. Chem. , 44 : 4396 Boeckman, R. K., Jr. private communication.

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