Total synthesis of murrastifoline-A by way of the Pd-catalyzed double N-arylation of a carbazolamine with a 2,2′-dibromobiphenyl derivative

Heterocycles

Volumn 65, Issue 7, 2005, Pages 1561-1567

  Kitawaki, Takafumi ^a   Hayashi, Yoko ^a   Chida, Noritaka ^a  

^a KEIO UNIVERSITY   (Japan)

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EID: 33646896293     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-05-10418     Document Type: Article

References (31)

1. Chakraborty D.P. In: Katritzky A.R. (Ed). The Alkaloids Vol. 44 (1993), Academic Press, Inc. 257-364
2. Knölker H.-J., and Reddy K.R. Chem. Rev. 102 (2002) 4303
3. Ito C., Wu T.-S., and Furukawa H. Chem. Pharm. Bull. 38 (1990) 1143
4. Ito C., and Furukawa H. Chem. Pharm. Bull. 38 (1990) 1548
5. Ito C., Thoyama Y., Omura M., Kajiura I., and Furukawa H. Chem. Pharm. Bull. 41 (1993) 2096
6. Furukawa H. Trends in Heterocyclic Chem. 3 (1993) 185
7. Tasler S., and Bringmann G. Chemical Record 2 (2002) 114
8. and references therein. Bringmann G., and Tasler S. Tetrahedron 57 (2001) 331
9. Bringmann G., Tasler S., Endress H., Kraus J., Messer K., Wohlfarth M., and Lobin W. J. Am. Chem. Soc. 123 (2001) 2703
10. Nozaki K., Takahashi K., Nakano K., Hiyama T., Tang H.-Z., Fujiki M., Yamaguchi S., and Tamao K. Angew. Chem. Int. Ed. 42 (2003) 2051
11. Kuwahara A., Nakano K., and Nozaki K. J. Org. Chem. 70 (2005) 413
12. Hartwig J.F. Angew. Chem., Int. Ed. 37 (1998) 2046
13. Yang B.H., and Buchwald S.L. J. Organomet. Chem. 576 (1999) 125
14. Harris M.C., and Buchwald S.L. J. Org. Chem. 65 (2000) 5327
15. Wolfe J.P., and Buchwald S.L. J. Org. Chem. 65 (2000) 1144
16. Zhang A., and Lin G. Bioorg. Med. Chem. Lett. 10 (2000) 1021
17. Lin G., and Zhang A. Tetrahedron 56 (2000) 7163
18. 13C NMR, IR and MS.
19. Miyaura N., and Suzuki A. Chem. Rev. 95 (1995) 2457
20. Suzuki A. J. Organomet. Chem. 576 (1999) 147
21. +), 420.1838; Found 420.1838.
22. Åkermark B., Eberson L., Jonsson E., and Pettersson E. J. Org. Chem. 40 (1975) 1365
23. and references therein. Knölker H.-J., and Knöll J. Chem. Commun. (2003) 1170
24. Methyl ether (14) would be formed by nucleophilic aromatic substitution reaction of compound (12) with methoxide ion. The similar substitution reactions, in which the bromo substituents in 1-bromo-3-methylcarbazole, 8-bromo-1,2,3,4-tetrahydrocarbazole, and 7-bromo-1,2,3,4-tetrahydrocarbazole were displaced with methoxy groups by treatment with sodium methoxide in the presence or absence of Cul, have been reported. See,. Kikugawa Y., Miyake Y., and Kawase M. Chem Pharm. Bull. 29 (1981) 1231
25. Kikugawa Y., Aoki Y., and Sakamoto T. J. Org. Chem. 66 (2001) 8612
26. Lalancette J.M., Frêche A., and Monteux R. Can. J. Chem. 46 (1968) 2754
27. Lalancette J.M., Frêche A., Brindle J.R., and Laliberté M. Synthesis (1972) 526
28. 2 in the presence of 5% Pd on carbon) resulted in the formation of many unidentified products. Panek J.S., Xu F., and Rondón A.C. J. Am. Chem. Soc. 120 (1998) 4113
29. Wolfe J.P., Tomori H., Sadighi J.P., Yin J., and Buchwald S.L. J. Org. Chem. 65 (2000) 1158
30. Wolfe J.P., and Buchwald S.L. Angew. Chem., Int. Ed. 38 (1999) 2413
31. 3 (7.8 mg, 8.5 μmol), 2-dicyclohexylphosphinobiphenyl (9.2 mg, 26 μol) and t-BuONa (8.2 mg, 85 μmol) in toluene (0.6 mL) for 10 min. The reaction mixture was then heated at 120 °C in a sealed tube for 24 h. After cooling, the mixture was purified by column chromatography (silica gel: 2 g, EtOAc / n-hexane = 1/30) to afford 15 (13.6 mg, 58%) as a syrup.