Simple Synthesis of 2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: A Key Intermediate for the Synthesis of 4-Demethoxydaunomycinone

(Note: The full text of this document is currently only available in the PDF Version )

Subhash P. Chavan, Y. Tripura Subbarao and Chittiboyina Amar Gopal


Abstract

2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene is prepared by using a 1,3-dipolar cycloaddition of nitrile oxide to the corresponding dihydronaphthalene.


References

  1. H. S. El Khadem, (Editor), Anthracycline Antibiotics, Academic Press, New York, 1982 Search PubMed; F. Arcamone, Doxerubicin Anticancer Antibiotics, Academic Press, New York, 1981 Search PubMed.
  2. F. Arcamone, L. Bernardi, P. Giardino, B. Patelli, A. DiMarco, A. M. Casazza, G. Pratesi and P. Reggiani, Cancer Treat. Rept., 1976, 60, 829 Search PubMed; S. Niedle, Nature (London), 1977, 268, 195.
  3. G. J. Thomas, in Recent Progress in the Chemical Synthesis of Antibiotics, Springer-Verlag, Berlin, Heidelberg, 1990, pp. 468–496 Search PubMed; K. Krohn, Tetrahedron, 1990, 46, 291 Search PubMed; Prog. Chem. Org. Nat. Prod., 1989, 55, 37 CrossRef CAS; Angew. Chem., Int. Ed. Engl., 1986, 25, 790 CrossRef CAS; M. J. Broadhurst, C. H. Hassall and G. J. Thomas, Chem. Ind. (London), 1985, 106 CrossRef CAS; T. R. Kelly, Tetrahedron, (Symposia in print 17), 1984, 40, 4537 Search PubMed.
  4. S. Terashima, K. Tanno and K. Koga, Tetrahedron Lett., 1980, 21, 2749 CrossRef CAS; A. V. Ramo Rao, V. H. Deshpande, B. Rammohan Rao and K. Ravichandran, Tetrahedron Lett., 1982, 23, 1115 CrossRef CAS; A. V. Rama Rao, J. S. Yadav, K. B. Reddy and A. R. Mehendale, Tetrahedron, 1984, 40, 4643 CrossRef CAS; M. P. Reddy and G. S. Krishna Rao, Tetrahedron Lett., 1981, 22, 3549 CrossRef CAS; R. A. Russell, G. J. Collin, P. S. Gee, A. S. Krauss and R. N. Warrener, Aust. J. Chem., 1984, 37, 1721 CAS.
  5. T. Mukaiyama and T. Hoshino, J. Am. Chem. Soc., 1960, 82, 5339 CrossRef CAS; G. Bianchi, C. De Micheli and R. Gandolfi, J. Chem. Soc., Perkin Trans. 1, 1976, 1518 RSC.
  6. D. P. Curran, J. Am. Chem. Soc., 1983, 105, 5826 CrossRef CAS.
  7. O. Diels and K. Alder, Chem. Ber., 1929, 62, 2337 Search PubMed.
  8. A. V. Rama Rao, V. H. Deshpande and N. Laxma Reddy, Tetrahedron Lett., 1982, 23, 4373 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.