Short synthetic route to 5,6-dihydroflavopereirine and flavopereirine

Heterocycles

Volumn 43, Issue 7, 1996, Pages 1365-1370

  Lounasmaa, Mauri ^a   Hanhinen, Pirjo ^a   Lipponen, Sami ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

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[No Author keywords available]

Indexed keywords

EID: 0007983335     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-7446     Document Type: Article

References (30)

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2. G. W. Gribble, "Studies in Natural Products Chemistry, Stereoselective Synthesis (Part A)", ed. by Atta-ur-Rahman, Vol. 1, Elsevier, Amsterdam, 1988, pp. 123-162 and references therein.
3. L. Angenot and A. Denoël, Planta Medica, 1973, 23, 226.
4. O. Bejar, R. Goutarel, M.-M. Janot, and A. Le Hir, C. R. Acad. Sci., 1957, 244, 2066. See also, A. Le Hir, M.-M. Janot, and D. van Stolk, Bull. Soc. Chim. Fr., 1958, 551.
5. O. Bejar, R. Goutarel, M.-M. Janot, and A. Le Hir, C. R. Acad. Sci., 1957, 244, 2066. See also, A. Le Hir, M.-M. Janot, and D. van Stolk, Bull. Soc. Chim. Fr., 1958, 551.
6. N. A. Hughes and H. Rapoport, J. Am. Chem. Soc., 1958, 80, 1604. See also, H. Rapoport, T. P. Onak, N. A. Hughes, and M. G. Reinecke, J. Am. Chem. Soc., 1958, 80, 1601.
7. N. A. Hughes and H. Rapoport, J. Am. Chem. Soc., 1958, 80, 1604. See also, H. Rapoport, T. P. Onak, N. A. Hughes, and M. G. Reinecke, J. Am. Chem. Soc., 1958, 80, 1601.
8. M. V. Kisakürek, A. J. M. Leeuwenberg, and M. Hesse, "Alkaloids: Chemical and Biological Perspectives", ed. by S. W. Pelletier, Vol. 1, Wiley, New York, 1983, p. 326.
9. E. Bächli, C. Vamvacas, H. Schmid, and P. Karrer, Helv. Chim. Acta, 1957, 40, 1167.
10. M. Lounasmaa, R. Jokela, B. Tirkkonen, J. Miettinen, and M. Halonen, Heterocycles, 1992, 34, 321.
11. 3COO-), 3.38 (1H, br d, J≈10 Hz, H-3), 3.45 (1H, d, J=16 Hz, H-
12. 2: C, 73.52, H, 7.14, N, 9.03. Found: C, 73.40, H, 7.06, N, 8.90.
13. 3OD (5 drops)]: 1.39 (3H, d, J=6.5 Hz, H-
14. 3COO-), 24.5 (C-14), 65.5 (C-5), 65.7 (C-3), 67.3 (C-21), 71.0 (C-19), 105.6 (C-7), 111.4 (C-12), 118.0 (C-9), 119.4 (C-10), 121.5 (C-11), 121.8 (C-15), 125.9 (C-8), 130.8* (C-
15. 3: C, 69.92, H, 6.79, N, 8.58. Found: C, 69.82, H, 6.90, N, 8.42.
16. P. Potier, Rev. Latinoamer. Quím., 1978, 9, 47.
17. M. Lounasmaa and A. Koskinen, Heterocycles, 1984, 22, 1591.
18. D. Grierson, "Organic Reactions", ed. by L. A. Paquette, Vol. 39, Wiley, New York, 1990, pp. 85-295.
19. 6): 1.38 (3H, t, J=7.5 Hz, H-18), 2.88 (2H, q, J=7.5 Hz, H-
20. +), 247 (100%).
21. M. Lounasmaa, P. Hanhinen, and R. Jokela, Heterocycles, 1996, 43, 443.
22. Compound (7). Yield 28%. For the analytical data, see Ref. 15.
23. Compound (8). Yield 12%. For the analytical data, see Ref. 15.
24. b-oxide (6) and its malonate analogue [Cf. compound (7) in Ref. 15] yield the same compounds (7 and 8) (vide supra), argues for similar mechanisms. This similarity, it may be added, furnishes supplementary evidence for the correctness of our preferred mechanism for the malonate analogue (Cf. Ref. 15, alternative two).
25. Compound (9). Yield 54%. For the analytical data, see Ref. 23.
26. V. S. Giri, B. C. Maiti, and S. C. Pakrashi, Heterocycles, 1984, 22, 233.
27. 13C Nmr signals marked with asterisks may be interchanged.
28. E. Wenkert, R. A. Massy-Westropp, and R. G. Lewis, J. Am. Chem. Soc., 1962, 84, 3732.
29. R. Jokela, A. Juntunen, and M. Lounasmaa, Planta Medica, 1987, 53, 386. See also, C. Kan-Fan and H.-P. Husson, Tetrahedron Lett., 1980, 21, 4265.
30. R. Jokela, A. Juntunen, and M. Lounasmaa, Planta Medica, 1987, 53, 386. See also, C. Kan-Fan and H.-P. Husson, Tetrahedron Lett., 1980, 21, 4265.