Acid-catalyzed rearrangements of flavan-4-phloroglucinol derivatives to novel 6-hydroxyphenyl-6a,11b-dihydro-6H-[1]benzofuro[2,3-c]-chromenes and hydroxyphenyl-3,2′-spirobi[dihydro[1]benzofurans]

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1997, Pages 2395-2403

  Steynberg, Petrus J ^a   Steynberg, Jan P ^a   Hemingway, Richard W ^a   Ferreira, Daneel ^b   McGraw, G Wayne ^c  

^a USDA FOREST SERVICE   (United States)

^b UNIVERSITY OF THE FREE STATE   (South Africa)

^c Louisiana College   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748648670     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a700889i     Document Type: Article

References (23)

1. K. D. Sears and R. L. Casebier, Chem. Commun., 1968, 1437.
2. B. R. Brown and M. R. Shaw, J. Chem. Soc., Perkin Trans. 1, 1974, 2036.
3. R. W. Hemingway, in Chemistry and Significance of Condensed Tannins, ed. R. W. Hemingway and J. J. Karchesy, Plenum Press, New York, 1989, p. 265.
4. R. K. Gupta and E. Haslam, J. Chem. Soc., Perkin Trans. 1, 1978, 892.
5. J. Regard, J. Perez-Ilzarbe, J. M. Ricardo da Silva and V. J. Cheynier, J. Chromatogr., 1991, 540, 401.
6. G. W. McGraw, J. P. Steynberg, T. G. Rials and R. W. Hemingway in Plant Polyphenols: Synthesis, Properties, Significance, ed. R. W. Hemingway and P. E. Laks, Plenum Press, New York, 1992, p. 979.
7. G. W. McGraw, J. P. Steynberg and R. W. Hemingway, Tetrahedron Lett., 1993, 34, 987.
8. R. W. Hemingway, L. Y. Foo, L. J. Porter, J. Chem. Soc., Perkin Trans. 1, 1982, 1209.
9. J. J. Botha, D. Ferreira and D. G. Roux, J. Chem. Soc., Chem. Commun., 1978, 698;
10. J. J. Botha, D. A. Young, D. Ferreira and D. G. Roux, J. Chem. Soc., Perkin Trans. 1, 1981, 1213.
11. M. W. Barrett, S. Klyne, P. M. Scopes, A. C. Fletcher, L. J. Porter and E. Haslam, J. Chem. Soc., Perkin Trans. 1, 1979, 2375.
12. L. J. Porter, in The Flavonoids: Advances in Research Since 1980, ed. J. B. Harborne, Chapman and Hall, London, 1988, p. 21.
13. R. W. Hemingway, in Natural Products of Woody Plants, ed. J. W. Rowe, Springer-Verlag, Berlin, 1989, p. 571.
14. H. Kolodziej, Phytochemistry, 1990, 29, 1671.
15. P. J. Steynberg, J. P. Steynberg and D. Ferreira, Tetrahedron, in the press;
16. P. J. Steynberg, PhD Thesis, University of the Orange Free State, South Africa, 1996.
17. J. H. Van der Westhuizen, D. Ferreira and D. G. Roux, J. Chem. Soc., Perkin Trans. 1, 1981, 1220.
18. P. K. Agrawal, M. C. Bansal, L. J. Porter and L. Y. Foo, in Carbon-13 NMR of Flavonoids, ed. P. K. Agrawal, Elsevier, Amsterdam, 1989, p. 432.
19. R. W. Hemingway, F. L. Tobiason, G. W. McGraw and J. P. Steynberg, Magn. Reson. Chem., 1996, 424.
20. P. W. Van Zyl, J. P. Steynberg, E. V. Brandt and D. Ferreria, Magn. Reson. Chem., 1993, 1057.
21. R. W. Hemingway, in Chemistry and Significance of Condensed Tannins, ed. R. W. Hemingway and J. J. Karchesy, Plenum Press, New York. 1989, p. 271.
22. L. J. Porter, R. Y. Wong, M. Benson, B. G. Chang, V. N. Viswanadhan, R. E. Gandour and W. L. Mattice, J. Chem. Res., 1986: (S), 86; (M), 830.
23. W. Peng, A. H. Conner and R. W. Hemingway, J. Wood Chem. Technol., in the press.