Transition metal complexes in organic synthesis. Part 62:[1] total synthesis of (±)-demethoxycarbonyldihydrogambirtannine and norketoyobyrine by an iron-mediated [2+2+1] cycloaddition

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5035-5038

  Knölker, Hans Joachim ^a   Cämmerer, Simon ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; GAMBIRTANNINE; KETOYOBYRINE; METAL COMPLEX; UNCLASSIFIED DRUG; YOHIMBAN DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; EXTRACT; INTOXICATION; NONHUMAN; OXIDATION; PLANT LEAF; REACTION ANALYSIS; SYNTHESIS;

EID: 0342588072     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00766-8     Document Type: Article

References (37)

1. Part 61: Knölker, H.-J.; Reddy, K. R. Tetrahedron 2000, 56, in press.
2. Merlini, L.; Mondelli, R.; Nasini, G.; Hesse, M. Tetrahedron 1967, 23, 3129.
3. Peube-Locou, N.; Plat, M.; Koch, M. Phytochemistry 1973, 12, 199.
4. Angenot, L.; Coune, C.; Tits, M. J. Pharm. Belg. 1978, 33, 284.
5. (a) Clemo, G.R.; Swan, G.A. J. Chem. Soc. 1946, 617.
6. (b) Schlittler, E.; Allemann, T. Helv. Chim. Acta 1948, 31, 128.
7. (c) Swan, G.A. J. Chem. Soc. 1949, 1720.
8. Beisler, J.A. Tetrahedron 1970, 26, 1961. Ninomiya, I.; Naito, T.; Takasugi, H. J. Chem. Soc., Perkin Trans. 1 1976, 1865. Meise, W.; Pfisterer, H. Arch. Pharm. 1977, 310, 501. Chatterjee, A.; Ghosh, S. Synthesis 1981, 818. Frostell, E.; Jokela, R.; Lounasmaa, M. Acta Chem. Scand. B 1981, 35, 671. Yamaguchi, R.; Otsuji, A.; Utimoto, K.; Kozima, S. Bull. Chem. Soc. Jpn. 1992, 65, 298.
9. Beisler, J.A. Tetrahedron 1970, 26, 1961. Ninomiya, I.; Naito, T.; Takasugi, H. J. Chem. Soc., Perkin Trans. 1 1976, 1865. Meise, W.; Pfisterer, H. Arch. Pharm. 1977, 310, 501. Chatterjee, A.; Ghosh, S. Synthesis 1981, 818. Frostell, E.; Jokela, R.; Lounasmaa, M. Acta Chem. Scand. B 1981, 35, 671. Yamaguchi, R.; Otsuji, A.; Utimoto, K.; Kozima, S. Bull. Chem. Soc. Jpn. 1992, 65, 298.
10. Beisler, J. A. Tetrahedron 1970, 26, 1961. Ninomiya, I.; Naito, T.; Takasugi, H. J. Chem. Soc., Perkin Trans. 1 1976, 1865. Meise, W.; Pfisterer, H. Arch. Pharm. 1977, 310, 501. Chatterjee, A.; Ghosh, S. Synthesis 1981, 818. Frostell, E.; Jokela, R.; Lounasmaa, M. Acta Chem. Scand. B 1981, 35, 671. Yamaguchi, R.; Otsuji, A.; Utimoto, K.; Kozima, S. Bull. Chem. Soc. Jpn. 1992, 65, 298.
11. Beisler, J.A. Tetrahedron 1970, 26, 1961. Ninomiya, I.; Naito, T.; Takasugi, H. J. Chem. Soc., Perkin Trans. 1 1976, 1865. Meise, W.; Pfisterer, H. Arch. Pharm. 1977, 310, 501. Chatterjee, A.; Ghosh, S. Synthesis 1981, 818. Frostell, E.; Jokela, R.; Lounasmaa, M. Acta Chem. Scand. B 1981, 35, 671. Yamaguchi, R.; Otsuji, A.; Utimoto, K.; Kozima, S. Bull. Chem. Soc. Jpn. 1992, 65, 298.
12. Beisler, J.A. Tetrahedron 1970, 26, 1961. Ninomiya, I.; Naito, T.; Takasugi, H. J. Chem. Soc., Perkin Trans. 1 1976, 1865. Meise, W.; Pfisterer, H. Arch. Pharm. 1977, 310, 501. Chatterjee, A.; Ghosh, S. Synthesis 1981, 818. Frostell, E.; Jokela, R.; Lounasmaa, M. Acta Chem. Scand. B 1981, 35, 671. Yamaguchi, R.; Otsuji, A.; Utimoto, K.; Kozima, S. Bull. Chem. Soc. Jpn. 1992, 65, 298.
13. Beisler, J. A. Tetrahedron 1970, 26, 1961. Ninomiya, I.; Naito, T.; Takasugi, H. J. Chem. Soc., Perkin Trans. 1 1976, 1865. Meise, W.; Pfisterer, H. Arch. Pharm. 1977, 310, 501. Chatterjee, A.; Ghosh, S. Synthesis 1981, 818. Frostell, E.; Jokela, R.; Lounasmaa, M. Acta Chem. Scand. B 1981, 35, 671. Yamaguchi, R.; Otsuji, A.; Utimoto, K.; Kozima, S. Bull. Chem. Soc. Jpn. 1992, 65, 298.
14. Knölker, H.-J. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, Chapter 3.13, p. 534. Knölker, H.-J. Chem. Soc. Rev. 1999, 28, 151.
15. Knölker, H.-J. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Eds.; Wiley-VCH: Weinheim, 1998; Vol. 1, Chapter 3.13, p. 534. Knölker, H.-J. Chem. Soc. Rev. 1999, 28, 151.
16. Weiss, E.; Hübel, W.; Merényi, R. Chem. Ber. 1962, 95, 1155. Weiss, E.; Merényi, R.; Hübel, W. Chem. Ber. 1962, 95, 1170. Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. Pearson, A. J.; Shively, R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096. Pearson, A. J.; Shively, R. J. Organometallics 1994, 13, 578.
17. Weiss, E.; Hübel, W.; Merényi, R. Chem. Ber. 1962, 95, 1155. Weiss, E.; Merényi, R.; Hübel, W. Chem. Ber. 1962, 95, 1170. Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. Pearson, A. J.; Shively, R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096. Pearson, A. J.; Shively, R. J. Organometallics 1994, 13, 578.
18. Weiss, E.; Hübel, W.; Merényi, R. Chem. Ber. 1962, 95, 1155. Weiss, E.; Merényi, R.; Hübel, W. Chem. Ber. 1962, 95, 1170. Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. Pearson, A. J.; Shively, R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096. Pearson, A. J.; Shively, R. J. Organometallics 1994, 13, 578.
19. Weiss, E.; Hübel, W.; Merényi, R. Chem. Ber. 1962, 95, 1155. Weiss, E.; Merényi, R.; Hübel, W. Chem. Ber. 1962, 95, 1170. Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. Pearson, A. J.; Shively, R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096. Pearson, A. J.; Shively, R. J. Organometallics 1994, 13, 578.
20. Weiss, E.; Hübel, W.; Merényi, R. Chem. Ber. 1962, 95, 1155. Weiss, E.; Merényi, R.; Hübel, W. Chem. Ber. 1962, 95, 1170. Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. Pearson, A. J.; Shively, R. J.; Dubbert, R. A. Organometallics 1992, 11, 4096. Pearson, A. J.; Shively, R. J. Organometallics 1994, 13, 578.
21. Knölker, H.-J.; Heber, J.; Mahler, C. H. Synlett 1992, 1002. Knölker, H.-J.; Heber, J. Synlett 1993, 924. Knölker, H.-J. J. Prakt. Chem. 1994, 336, 277.
22. Knölker, H.-J.; Heber, J.; Mahler, C. H. Synlett 1992, 1002. Knölker, H.-J.; Heber, J. Synlett 1993, 924. Knölker, H.-J. J. Prakt. Chem. 1994, 336, 277.
23. Knölker, H.-J.; Heber, J.; Mahler, C. H. Synlett 1992, 1002. Knölker, H.-J.; Heber, J. Synlett 1993, 924. Knölker, H.-J. J. Prakt. Chem. 1994, 336, 277.
24. Shvo, Y.; Hazum, E. J. Chem. Soc., Chem. Commun. 1974, 336. Knölker, H.-J. J. Prakt. Chem. 1996, 338, 190.
25. Shvo, Y.; Hazum, E. J. Chem. Soc., Chem. Commun. 1974, 336. Knölker, H.-J. J. Prakt. Chem. 1996, 338, 190.
26. Knölker, H.-J.; Goesmann, H.; Klauss, R. Angew. Chem. 1999, 111, 727; Angew. Chem., Int. Ed. 1999, 38, 702.
27. Knölker, H.-J.; Goesmann, H.; Klauss, R. Angew. Chem. 1999, 111, 727; Angew. Chem., Int. Ed. 1999, 38, 702.
28. Knölker, H.-J.; Baum, E.; Goesmann, H.; Klauss, R. Angew. Chem. 1999, 111, 2196; Angew. Chem., Int. Ed. 1999, 38, 2064.
29. Knölker, H.-J.; Baum, E.; Goesmann, H.; Klauss, R. Angew. Chem. 1999, 111, 2196; Angew. Chem., Int. Ed. 1999, 38, 2064.
30. Ogliaruso, M. A.; Romanelli, M. G.; Becker, E. I. Chem. Rev. 1965, 65, 261.
31. Knölker, H.-J.; Baum, E.; Heber, J. Tetrahedron Lett. 1995, 36, 7647.
32. Knölker, H.-J.; Braier, A.; Bröcher, D. J.; Jones, P. G.; Piotrowski, H. Tetrahedron Lett. 1999, 40, 8075.
33. Whittaker, N. J. Chem. Soc. C 1969, 85.
34. Kawate, T.; Nakagawa, M.; Yamazaki, H.; Hirayama, M.; Hino, T. Chem. Pharm. Bull. 1993, 41, 287.
35. Bohlmann, F. Chem. Ber. 1958, 91, 2157.
36. Uskokovic, M.; Bruderer, H.; von Planta, C.; Williams, T.; Brossi, A. J. Am. Chem. Soc. 1964, 86, 3364.
37. 2: C, 83.18; H, 6.61; N, 10.21; found: C, 83.00; H, 6.57; N, 10.42.