A New Two-Step Synthesis of Quinolone Alkaloids Based on the Regioselective Addition of Organometallic Reagents to 4-Silyloxyquinolinium Triflates

Synlett

Volumn 1997, Issue 3, 1997, Pages 313-315

  Beifuss, Uwe ^a   Ledderhose, Sabine ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001802885     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-758     Document Type: Article

References (43)

1. (a) Michael, J. P. Nat. Prod. Rep. 1995, 12, 77.
2. (b) Grundon, M. F. In The Alkaloids, Vol. 32; Brossi, A., Ed.; Academic Press: San Diego, 1988, p 341.
3. (a) Review: Radl, S.; Bouzard, D. Heterocycles 1992, 34, 2143.
4. (b) Graybill, T. L.; Dolle, R. E.; Osifo, I. K.; Schmidt, S. J.; Gregory, J. S.; Harris, A. L.; Miller, M. S. Bioorg. Med. Chem. Lett. 1995, 5, 387.
5. (c) Wentland, M. P.; Lesher, G. Y.; Reuman, M.; Gruett, M. D.; Singh, B.; Aldous, S. C.; Dorff, P. H.; Rake, J. B.; Coughlin, S. A. J. Med. Chem. 1993, 36, 2801.
6. (d) Kuo, S.-C.; Lee, H.-Z.; Juang, J.-P.; Lin, Y.-T.; Wu, T.-S.; Chang, J.-J.; Lednicer, D.; Paull, K. D.; Lin, C. M.; Hamel, E.; Lee, K.-H. J. Med. Chem. 1993, 36, 1146.
7. (e) Leeson, P. D.; Baker, R.; Carling, R. W.; Curtis, N. R.; Moore, K. W.; Williams, B. J.; Foster, S. C.; Donald, A. E.; Kemp, J. A.; Marshall, G. R. J. Med. Chem. 1991, 34, 1243.
8. Reimann, E. In Houben-Weyl, 4th ed., Vol. E7a/2; Kreher, R. P., Ed.; Thieme: Stuttgart, 1991, p 290.
9. (a) Tollari, S.; Cenini, S.; Ragaini, F.; Cassar, L. J. Chem. Soc., Chem. Commun. 1994, 1741.
10. (b) Torii, S.; Okumoto, H.; Xu, L. H.; Sadakane, M.; Shostakovsky, M. V.; Ponomaryov, A. B.; Kalinin, V. N. Tetrahedron 1993,49, 6773.
11. (c) Chen, B.; Huang, X.; Wang, J. Synthesis 1987, 482.
12. Reviews: (a) Reimann, E. In Houben-Weyl, 4th ed., Vol. E7a/2; Kreher, R. P., Ed.; Thieme: Stuttgart, 1991; p 542. (b) Keay, J. G. In Adv. Heterocycl. Chem., Vol. 39; Katritzky, A. R., Ed.; Academic Press: London, 1986; p 1. (c) Pilyugin, G. T.; Gutsulyak, B. M. Russ. Chem. Rev. 1963, 32, 167.
13. Reviews: (a) Reimann, E. In Houben-Weyl, 4th ed., Vol. E7a/2; Kreher, R. P., Ed.; Thieme: Stuttgart, 1991; p 542. (b) Keay, J. G. In Adv. Heterocycl. Chem., Vol. 39; Katritzky, A. R., Ed.; Academic Press: London, 1986; p 1. (c) Pilyugin, G. T.; Gutsulyak, B. M. Russ. Chem. Rev. 1963, 32, 167.
14. Reviews: (a) Reimann, E. In Houben-Weyl, 4th ed., Vol. E7a/2; Kreher, R. P., Ed.; Thieme: Stuttgart, 1991; p 542. (b) Keay, J. G. In Adv. Heterocycl. Chem., Vol. 39; Katritzky, A. R., Ed.; Academic Press: London, 1986; p 1. (c) Pilyugin, G. T.; Gutsulyak, B. M. Russ. Chem. Rev. 1963, 32, 167.
15. For leading references: (a) Diaba, F.; Lewis, I.; Grignon-Dubois, M.; Navarre, S. J. Org. Chem. 1996, 61, 4830. (b) Fukuzumi, S.; Noura, S. J. Chem. Soc., Chem. Commun. 1994, 287. (c) Akiba, K.; Kasai, T.; Wada, M. Tetrahedron Lett. 1982, 23, 1709. (d) Popp, F. D. In The Chemistry of Heterocyclic Compounds: Quinolines, part II; Jones, G., Ed.; John Wiley & Sons: New York, 1982, p 353. (e) Schultz, O.-E.; Amschler, U. Liebigs Ann. Chem. 1970, 740, 192. (f) Bradley, W.; Jeffrey, S. J. Chem. Soc. 1954, 2770. (g) Leonard, N. J.; Foster, R. L. J. Am. Chem. Soc. 1952, 74, 3671.
16. For leading references: (a) Diaba, F.; Lewis, I.; Grignon-Dubois, M.; Navarre, S. J. Org. Chem. 1996, 61, 4830. (b) Fukuzumi, S.; Noura, S. J. Chem. Soc., Chem. Commun. 1994, 287. (c) Akiba, K.; Kasai, T.; Wada, M. Tetrahedron Lett. 1982, 23, 1709. (d) Popp, F. D. In The Chemistry of Heterocyclic Compounds: Quinolines, part II; Jones, G., Ed.; John Wiley & Sons: New York, 1982, p 353. (e) Schultz, O.-E.; Amschler, U. Liebigs Ann. Chem. 1970, 740, 192. (f) Bradley, W.; Jeffrey, S. J. Chem. Soc. 1954, 2770. (g) Leonard, N. J.; Foster, R. L. J. Am. Chem. Soc. 1952, 74, 3671.
17. For leading references: (a) Diaba, F.; Lewis, I.; Grignon-Dubois, M.; Navarre, S. J. Org. Chem. 1996, 61, 4830. (b) Fukuzumi, S.; Noura, S. J. Chem. Soc., Chem. Commun. 1994, 287. (c) Akiba, K.; Kasai, T.; Wada, M. Tetrahedron Lett. 1982, 23, 1709. (d) Popp, F. D. In The Chemistry of Heterocyclic Compounds: Quinolines, part II; Jones, G., Ed.; John Wiley & Sons: New York, 1982, p 353. (e) Schultz, O.-E.; Amschler, U. Liebigs Ann. Chem. 1970, 740, 192. (f) Bradley, W.; Jeffrey, S. J. Chem. Soc. 1954, 2770. (g) Leonard, N. J.; Foster, R. L. J. Am. Chem. Soc. 1952, 74, 3671.
18. For leading references: (a) Diaba, F.; Lewis, I.; Grignon-Dubois, M.; Navarre, S. J. Org. Chem. 1996, 61, 4830. (b) Fukuzumi, S.; Noura, S. J. Chem. Soc., Chem. Commun. 1994, 287. (c) Akiba, K.; Kasai, T.; Wada, M. Tetrahedron Lett. 1982, 23, 1709. (d) Popp, F. D. In The Chemistry of Heterocyclic Compounds: Quinolines, part II; Jones, G., Ed.; John Wiley & Sons: New York, 1982, p 353. (e) Schultz, O.-E.; Amschler, U. Liebigs Ann. Chem. 1970, 740, 192. (f) Bradley, W.; Jeffrey, S. J. Chem. Soc. 1954, 2770. (g) Leonard, N. J.; Foster, R. L. J. Am. Chem. Soc. 1952, 74, 3671.
19. For leading references: (a) Diaba, F.; Lewis, I.; Grignon-Dubois, M.; Navarre, S. J. Org. Chem. 1996, 61, 4830. (b) Fukuzumi, S.; Noura, S. J. Chem. Soc., Chem. Commun. 1994, 287. (c) Akiba, K.; Kasai, T.; Wada, M. Tetrahedron Lett. 1982, 23, 1709. (d) Popp, F. D. In The Chemistry of Heterocyclic Compounds: Quinolines, part II; Jones, G., Ed.; John Wiley & Sons: New York, 1982, p 353. (e) Schultz, O.-E.; Amschler, U. Liebigs Ann. Chem. 1970, 740, 192. (f) Bradley, W.; Jeffrey, S. J. Chem. Soc. 1954, 2770. (g) Leonard, N. J.; Foster, R. L. J. Am. Chem. Soc. 1952, 74, 3671.
20. For leading references: (a) Diaba, F.; Lewis, I.; Grignon-Dubois, M.; Navarre, S. J. Org. Chem. 1996, 61, 4830. (b) Fukuzumi, S.; Noura, S. J. Chem. Soc., Chem. Commun. 1994, 287. (c) Akiba, K.; Kasai, T.; Wada, M. Tetrahedron Lett. 1982, 23, 1709. (d) Popp, F. D. In The Chemistry of Heterocyclic Compounds: Quinolines, part II; Jones, G., Ed.; John Wiley & Sons: New York, 1982, p 353. (e) Schultz, O.-E.; Amschler, U. Liebigs Ann. Chem. 1970, 740, 192. (f) Bradley, W.; Jeffrey, S. J. Chem. Soc. 1954, 2770. (g) Leonard, N. J.; Foster, R. L. J. Am. Chem. Soc. 1952, 74, 3671.
21. For leading references: (a) Diaba, F.; Lewis, I.; Grignon-Dubois, M.; Navarre, S. J. Org. Chem. 1996, 61, 4830. (b) Fukuzumi, S.; Noura, S. J. Chem. Soc., Chem. Commun. 1994, 287. (c) Akiba, K.; Kasai, T.; Wada, M. Tetrahedron Lett. 1982, 23, 1709. (d) Popp, F. D. In The Chemistry of Heterocyclic Compounds: Quinolines, part II; Jones, G., Ed.; John Wiley & Sons: New York, 1982, p 353. (e) Schultz, O.-E.; Amschler, U. Liebigs Ann. Chem. 1970, 740, 192. (f) Bradley, W.; Jeffrey, S. J. Chem. Soc. 1954, 2770. (g) Leonard, N. J.; Foster, R. L. J. Am. Chem. Soc. 1952, 74, 3671.
22. (a) Beifuss, U.; Gehm, H.; Noltemeyer, M.; Schmidt, H.-G. Angew. Chem. 1995, 107, 705; Angew. Chem., Int. Ed. Engl. 1995, 34, 647.
23. (a) Beifuss, U.; Gehm, H.; Noltemeyer, M.; Schmidt, H.-G. Angew. Chem. 1995, 107, 705; Angew. Chem., Int. Ed. Engl. 1995, 34, 647.
24. (b) Beifuss, U.; Ledderhose, S. Synlett 1995, 938.
25. (c) Beifuss, U.; Tietze, M.; Gehm, H. Synlett 1996, 182.
26. 13C NMR, IR, UV, and MS) data were obtained for all new compounds.
27. (a) Meghani, P.; Joule, J. A. J. Chem. Soc., Perkin Trans, 1 1988, 1.
28. (b) Cassis, R.; Tapia, R.; Valderrama. J. A. Synth. Commun. 1985, 15, 125.
29. General Experimental Procedure for the synthesis of 5,6: A mixture of the N-protected quinolone 1,2 (1.00 mmol) and TIPSOTf (0.54 mL, 2.00 mmol) was treated under argon without stirring for 1 h at rt. Dichloromethane (5 mL), 2,6-lutidine (0.22 mL, 2.00 mmol) and the appropriate organometallic species (2.00-5.00 equiv.) were added at the temp. given in Scheme 1. The Grignard reagents were added as 1 M solutions in THF. The solution was stirred until completion (TLC) and quenched with ice (5 g). After extraction with dichloromethane (2 × 10 mL) the combined organic layers were dried over sodium sulfate, the solvent was removed in vacuo and the residue purified by flash chromatography on silica gel.
30. 5).
31. br, J = 8.0 Hz, 1H, 8-H), 8.04 (ddd, J = 0.5 Hz, J = 2.0 Hz, J = 8.0 Hz, 1H, 5-H).
32. (a) Evans, P. A.; Longmire, J. M.; Modi, D. P. Tetrahedron Lett. 1995, 36, 3985.
33. (b) Comins, D. L.; Joseph, S. P.; Peters, D. D. Tetrahedron Lett. 1995, 36, 9449.
34. (c) Larock, R. C.; Hightower, T. R.; Kraus, G. A.; Hahn, P.; Zheng, D. Tetrahedron Lett. 1995, 36, 2423.
35. (d) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
36. (e) Fleming, I.; Paterson, I. Synthesis 1979, 736.
37. (f) Ito, Y.; Hirao, T.; Saegusa, T. J. Org. Chem. 1978, 43, 1011.
38. (g) Friedrich, E.; Lutz, W. Angew. Chem. 1977, 89, 426; Angew. Chem., Int. Ed. Engl. 1977, 16, 413.
39. (g) Friedrich, E.; Lutz, W. Angew. Chem. 1977, 89, 426; Angew. Chem., Int. Ed. Engl. 1977, 16, 413.
40. (h) Jung, M. E.; Pan, Y.-G.; Rathke, M. W.; Sullivan, D. F. J. Org. Chem. 1977, 42, 3961.
41. Southon, I. W.; Buckingham, J. Dictionary of Alkaloids; Chapman and Hall: London, 1989.
42. General Experimental Procedure for the synthesis of 8: The appropriate silyl enol ether 6 (0.50 mmol) was suspended in dry methanol (10 mL) and under an atmosphere of hydrogen a catalytic amount of 10% Pd/C was added. The suspension was stirred at 20 °C until completion (TLC) and filtered over Celite. The filter aid was washed with methanol (5 mL). The solvent was removed in vacuo and the crude product was washed with diethyl ether (1 × 5 mL) to obtain pure 8.
43. 3), 23.40 (C-4′), 29.86 (C-3′), 32.42 (C-2′), 34.94 (C-1′), 108.78 (C-3), 119.05 (C-8), 124.97 (C-6), 125.45 (C-4a), 125.92 (C-5), 133.30 (C-7), 141.54 (C-8a), 157.02 (C-2), 180.53 (C-4).