Studies on the Synthesis of Highly Substituted Naphthol: Preparation of 6-Hydroxy-5,7-dimethoxy-2-naphthoic Acid, Isolated from Ulmus Thomasii

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

Claudio Fuganti and Stefano Serra


Abstract

An improvement to a known procedure, affording substituted 4-hydroxy-2-naphthoic acid derivatives from aromatic aldehydes, is described and its general applicability shown through the preparation of a natural naphthalene derivative isolated from Ulmus thomasii.


References

  1. E. Brenna, C. Fuganti, V. Perozzo and S. Serra, Tetrahedron, 1997, 53, 15029 CrossRef CAS.
  2. For a review on the aromatic annulation reaction see: P. Bamfield and P. F. Gordon, Chem. Soc. Rev., 1984, 13, 441 Search PubMed for more recent examples in the field of fused ring systems see: A. R. Katritzky, G. Zhang and L. Xie, J. Org. Chem., 1997, 62, 721 RSC; A. R. Katritzky, C. N. Fali and J. Li, J. Org. Chem., 1997, 62, 8205 Search PubMed.
  3. For a previous annulation method involving dienylketenes see: P. Turnbull and H. W. Moore, J. Org. Chem., 1995, 60, 644 Search PubMed and references cited therein S. Karady, J. S. Amato, R. A. Reamer and L. M. Weinstock, Tetrahedron Lett., 1996, 37, 8277 CrossRef CAS.
  4. E. Brenna, C. Fuganti and S. Serra, Tetrahedron, 1998, 54, 1585 CrossRef CAS.
  5. F. D. Hostettler and M. K. Seikel, Tetrahedron, 1969, 25, 2325 CrossRef CAS; C. Loung Chen and F. D. Hostettler, Tetrahedron, 1969, 25, 3223 CrossRef CAS; J. L. Charlton and K. Ann Lee, Tetrahedron Lett., 1997, 38, 7311 CrossRef CAS.
  6. M. Lehrer and R. Stevenson, J. Chem. Soc., Perkin Trans. 1, 1974, 1165 RSC.
  7. B. A. Pearlman, J. M. McNamara, I. Hasan, S. Hatakeyama, H. Sekizaki and Y. Kishi, J. Am. Chem. Soc., 1981, 103, 4248 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.