The regiospecific synthesis of angularly-fused xanthones via the benzannulation of 1,2-adducts derived from 3-(o-anisoyl)-4-substituted cyclobutenediones and their dithianyl derivatives.

Tetrahedron Letters

Volumn 38, Issue 21, 1997, Pages 3663-3666

  Sun, Lijun ^a   Liebeskind, Lanny S ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

Cyclobutenedione; Dithiane; Vinylketene; Xanthone

Indexed keywords

XANTHONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030940906     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00720-X     Document Type: Article

References (33)

1. Roberts, J. C. Chem, Rev. 1961, 591.
2. Afzal, M.; Al-Hassan, J. M. Heterocycles 1980, 14, 1173.
3. Sultanbawa, M. U. S. Tetrahedron 1980, 36, 1465.
4. Bennett, G. J.; Lee, H.-H. Phytochemistry 1989, 28, 967.
5. Hostettmann, K.; Hostettmann, M. In Methods in Plant Biochemistry; Harborne, J. B., Ed.; Academic Press: London, 1989; Vol. 1; pp 493.
6. Sordat-Diserens, I.; Marston, A.; Hamburger, M.; Rogers, C.; Hostettmann, K. Helv. Chim. Acta 1989, 72, 1001.
7. Sordat-Diserens, I.; Hamburger, M.; Rogers, C.; Hostettmann, K. Phytochemistry 1992, 31, 3589.
8. Nishikawa, H.; Robinson, R. J. Chem. Soc. 1922, 121, 839.
9. Findlay, J. W. A.; Gupta, P.; Lewis, J. R. J. Chem. Soc. (C) 1969, 2761.
10. Royer, R.; Lechartier, J. P.; Demerseman, P. Bull. Soc. Chim. Fr. 1972, 2948.
11. Quillinan, A. J.; Scheinmann, F. J. Chem. Soc., Perkin Trans. I 1973, 1329.
12. Ho, D. K.; McKenzie, A. T.; Byrn, S. R.; Cassady, J. M. J. Org. Chem. 1987, 52, 342.
13. Hauser, F. M.; Hewawasam, P.; Baghadanov, V. M. J. Org. Chem. 1988, 53, 223.
14. Kelly, T. R.; Jagoe, C. T.; Li, Q. J. Am. Chem. Soc. 1989, 111, 4522.
15. Mehta, G.; Shah, S. R. Tetrahedron Lett. 1991, 32, 5195.
16. Rao, A. V. R.; Yadav, J. S.; Reddy, K. K.; Upender, V. Tetrahedron Lett. 1991, 32, 5199.
17. Patek, M.; Lebl, M.; Budesinsky, M. Tetrahedron Lett. 1992, 33, 4507.
18. Hormi, O. E. O.; Hirvelä, L. Tetrahedron Lett. 1993, 34, 6463.
19. Kondedeshmukh, R. S.; Paradkar, M. V. Synth. Commun. 1994, 24, 659.
20. Sun, L.; Liebeskind, L. S. J. Am. Chem. Soc. 1996, 118, 12473.
21. Liebeskind, L. S. Tetrahedron Symposium in Print 1989, 45, 3053.
22. Moore, H. W.; Yerxa, B. R. Chemtracts - Organic Chemistry 1992, 5, 273.
23. Liebeskind, L. S.; Wang, J. Y. J. Org. Chem. 1993, 58, 3550.
24. Gurski-Birchler, A.; Liu, F.; Liebeskind, L. S. J. Org. Chem. 1994, 59, 7737.
25. Koo, S.; Liebeskind, L. S. J. Am. Chem. Soc. 1995, 117, 3389.
26. Turnbull, P.; Moore, H. W. J. Org. Chem, 1995, 60, 3274.
27. 13C NMR, and elemental analysis (less than +/-0.3% of C, H, N and/or S).
28. Sun, L.; Liebeskind, L. S. J. Org. Chem. 1995, 60, 8194.
29. 13C NMR spectroscopy and elemental analysis (±0.3% of C, H, N and/or S).
30. Liebeskind, L. S.; Yu, M. S.; Fengl, R. W. J. Org. Chem. 1993, 58, 3543.
31. A full study of the use of 3-(1,3-dithian-2-yl)-4-substituted-3-cyclobutene-1,2-diones as synthetic equivalents of 3-acyl-4-substituted-3-cyclobutene-1,2-diones in benzannulation reactions has been completed and will be disclosed in due course (L. Sun and L. S. Liebeskind, J. Org. Chem. to be submitted).
32. The regiochemistry of the nucleophilic addition was assigned on the basis of two factors: (1) Nucleophilic addition to cyclobutenediones is known to occur with high regioselectivity at the non-vinylogous ester (or vinylogous amide) carbonyl group, and (2) an extensive but yet unpublished study has demonstrated highly selective nucleophilic attack at the cyclobutenedione carbonyl group most distant from sterically encumbering substituents at the 3-or 4-position of the cyclobutenedione ring.
33. Grobel, B.-T.; Seebach, D. Synthesis 1977, 357.