Direct synthesis of pterocarpans via aldol condensation of phenylacetates with benzaldehydes

Tetrahedron

Volumn 55, Issue 40, 1999, Pages 11773-11786

  Van Aardt, Theunis G ^a   Van Rensburg, Hendrik ^a   Ferreira, Daneel ^b  

^a UNIVERSITY OF THE FREE STATE   (South Africa)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

Aldol condensation; Isoflavonoids; Pterocarpans

Indexed keywords

BENZALDEHYDE; ISOFLAVONOID; NATURAL PRODUCT; PHENYLACETIC ACID; PTEROCARPAN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ISOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0033214465     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00679-1     Document Type: Article

References (35)

1. Dewick, P.M. in The Flavonoids, Advances in Research since 1986, ed. Harborne, J.B., Chapman & Hall, London, 1994, pp. 166-178.
2. Mansfield, J.W. in Phytoalexins, ed. Bailey, J.A., Mansfield, J.W., Blackie & Son Ltd., Glasgow and London, 1982, pp. 289-312.
3. Nakagawa, M.; Nakanishi, K. Darko, L.L,; Vick, J.A., Tetrahedron Lett., 1982, 23, 3855-3858.
4. Máximo, P.; Lourenço, A. Phytochemistry, 1998, 48, 359-362.
5. Perrin, D.R. Tetrahedron Lett., 1964, 1, 29-35.
6. Ingham, J. L. in Progress in the Chemistry of Organic Natural Products, ed. Herz, W., Grisebach, H., Kirby, G. W., Springer-Verlag, New York, 1983, 43, pp. 1-266.
7. Ishiguro, M.; Tatsuoka, T.; Nakatsuka, N. Tetrahedron Lett., 1982, 23, 3859-3862.
8. Narkhede, D.D.; Iyer, P.R.; Iyer, C.S.R. Tetrahedron, 1990, 46, 2031-2034.
9. Krishna Prasad, A.V.; Kapil, R.S.; Popli, S.P. J. Chem. Soc., Perkin Trans I, 1986, 1561-1563.
10. Engler, T.A.; Reddy, J.P.; Combrink, K.D.; Vander Velde, D. J. Org. Chem., 1990, 55, 1248-1254.
11. Subburaj, K.; Murugesh, M.G.; Trivedi, G.K. J. Chem. Soc., Perkin Trans I, 1997, 1875-1878.
12. Ozaki, Y.; Mochida, K.; Kim, S.-W. J. Chem. Soc., Chem. Commun., 1988, 374-375.
13. Ozaki, Y.; Mochida, K.; Kim, S.-W. J. Chem. Soc., Perkin Trans I, 1989, 1219-1224.
14. Pinard, E.; Gaudry, M.; Hénot, F.; Thellend, A. Tetrahedron Lett., 1998, 39, 2739-2742.
15. Engler, T.A.; Letavic, M.A.; Reddy, J.P. J. Am. Chem. Soc., 1991, 113, 5068-5070.
16. Engler, T.A.; Letavic, M.A.; Iyengar, R.; La Tessa, K.O.; Reddy, J.P. J. Org. Chem., 1999, 64, 2391-2405.
17. Van Aardt, T.G.; Van Heerden, P.S.; Ferreira, D. Tetrahedron Lett., 1998, 39, 3881-3884.
18. Auerbach, J.; Weinreb, S.M. J. Chem. Soc., Chem. Commun., 1974, 298-299.
19. Van Rensburg, H.; Van Heerden, P.S.; Bezuidenhoudt, B.C.B.; Ferreira, D. J. Chem. Soc., Chem. Commun., 1996, 2747-2748.
20. Greene, T.W. in Protective Groups in Organic Synthesis, John Wiley & Sons, New York, 1981,100-101.
21. McKillop, A.; Swann, B.P.; Taylor, E.C. J. Am. Chem. Soc., 1973, 95, 3340-3343.
22. Paterson, I.; Goodman, J.M. Tetrahedron Lett., 1989, 30, 997-1000.
23. Meyers, A.I.; Reider, P.J. J. Am. Chem. Soc., 1979, 101, 2501-2502.
24. Pirrung, M.C.; Heathcock, C.H. J.Org. Chem., 1980, 45, 1727-1728.
25. Heathcock, C.H.; Buse, C.T.; Kleschick, W.A.; Pirrung, M.C.; Sohn, J.E.; Lampe, J. J. Org. Chem., 1980, 45, 1066-1081.
26. Mitsunobu. O. Synthesis, 1981, 1-28.
27. Clark, J.H. J. Chem. Soc., Chem. Commun., 1978, 789-791.
28. Trost, B.M.; Murayama, E. J. Am. Chem. Soc., 1981, 103, 6529-6530.
29. Trost, B.M.; Sato, T. J. Am. Chem. Soc., 1985, 107, 719-721.
30. Williams, R.M.; Armstrong, R.W.; Dung, J-S. J. Am. Chem. Soc., 1984, 106, 5748-5750.
31. Roush, W.R. J. Org. Chem., 1991, 56, 4151-4157.
32. Evans, D.A.; Nelson, J.V.; Vogel, E.; Taber, T.R. J. Am. Chem. Soc., 1981, 103, 3099-3111.
33. Stiles, M.; Winkler, R.R.; Chang, Y-L.; Traynor, L. J. Am. Chem. Soc., 1964, 86, 3337-3342.
34. Tobiason, F.L.; Hemingway, R.W. Tetrahedron Lett., 1994, 35, 2137.
35. Suginome, H.; Iwadare, T. Experientia, 1962, 18, 163-164.