Enantioselective synthesis of the trans-2,6-dialkylpiperidine alkaloids (2R,6R)-lupetidine and (2R,6R)-solenopsin A

Tetrahedron Asymmetry

Volumn 9, Issue 14, 1998, Pages 2419-2422

  Amat, Mercedes ^a   Hidalgo, José ^a   Llor, Núria ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

NANOFIN; PIPERIDINE DERIVATIVE; SOLENOPSIN A; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; COLUMN CHROMATOGRAPHY; DERIVATIZATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032540967     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00249-3     Document Type: Article

References (65)

1. 1. (a) Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1985; Vol. 3, pp. 1-90.
2. (b) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1985; Vol. 26, pp. 89-183.
3. (c) Wang, C.-L. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 585-621.
4. (d) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science: Amsterdam, 1995; Vol. 16, pp. 453-502.
5. (e) Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996; Vol. 10, pp. 155-299.
6. 2. (a) MacConnell, J. G.; Blum, M. S.; Fales, H. M. Tetrahedron 1971, 26, 1129-1139.
7. (b) Jones, T. H.; Blum, M. S.; Fales, H. M. Tetrahedron 1982, 38, 1949-1958.
8. (c) Leclercq, S.; Thirionet, I.; Broeders, F.; Daloze, D.; Vander Meer, R.; Braekman, J. C. Tetrahedron 1994, 50, 8465-8478.
9. 3. For a review, see: Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Proced. Int. 1996, 28, 501-543.
10. 4. (a) Hill, R. K.; Yuri, T. Tetrahedron 1977, 33, 1569-1571.
11. (b) Sakane, S.; Matsumura, Y.; Yamamura, Y.; Ishida, Y.; Maruoka, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 672-674.
12. (c) Maruoka, K.; Miyazaki, T.; Ando, M.; Matsumura, Y.; Sakane, S.; Hattori, K.; Yamamoto, H. J. Am. Chem. Soc. 1983, 105, 2831-2843.
13. (d) Meyers, A. I.; Edwards, P. D.; Bailey, T. R.; Jagdmann, G. E. J. Org. Chem. 1985, 50, 1019-1026.
14. (e) Yamaguchi, R.; Nakazono, Y.; Matsuki, T.; Hata, E.; Kawanisi, M. Bull. Chem. Soc. Jpn 1987, 60, 215-222.
15. (f) Ryckman, D. M.; Stevens, R. V. J. Org. Chem. 1987, 52, 4274-4279.
16. (g) Taber, D. F.; Deker, P. B.; Fales, H. M.; Jones, T. H.; Lloyd, H. A. J. Org. Chem. 1988, 53, 2968-2971.
17. (h) Bacos, D.; Célérier, J. P.; Marx, E.; Rosset, S.; Lhommet, G. J. Heterocyclic Chem. 1990, 27, 1387-1392.
18. (i) Fukuda, Y.; Utimoto, K. Synthesis 1991, 975-978.
19. (j) Fukuda, Y.; Matsubara, S.; Utimoto, K. J. Org. Chem. 1991, 56, 5812-5816.
20. (k) Ukaji, Y.; Watai, T.; Sumi, T.; Fujisawa, T. Chem. Lett. 1991, 1555-1558.
21. 5. (a) Bonin, M.; Romero, J. R.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1982, 23, 3369-3372.
22. (b) Takahashi, K.; Kurita, H.; Ogura, K.; Iida, H. J. Org. Chem. 1985, 50, 4368-4371.
23. (c) Grierson, D. S.; Royer, J.; Guerier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475-4477.
24. (d) Wasserman, H. H.; Rusiecki, V. Tetrahedron Lett. 1988, 29, 4977-4980.
25. (e) Comins, D. L.; Weglarz, M. A. J. Org. Chem. 1991, 56, 2506-2512.
26. (f) Kotsuki, H.; Kusumi, T.; Inoue, M.; Ushio, Y.; Ochi, M. Tetrahedron Lett. 1991, 32, 4159-4162.
27. (g) Jefford, C. W.; Bo Wang, J. Tetrahedron Lett. 1993, 34, 2911-2914.
28. 6. (a) Moriyama, Y.; Doan-Huynh, D.; Monneret, C.; Khuong-Huu, Q. Tetrahedron Lett. 1977, 825-828.
29. (b) Adams, D. R.; Carruthers, W.; Williams, M. J.; Crowley, P. J. J. Chem. Soc., Perkin Trans. 1 1989, 1507-1513.
30. (c) Mundy, B. P.; Bjorklund, M. Tetrahedron Lett. 1985, 26, 3899-3902.
31. (d) Padwa, A.; Fryxell, G. E.; Zhi, L. J. Am. Chem. Soc. 1990, 112, 3100-3109.
32. 7. (a) Carruthers, W.; Williams, M. J. J. Chem. Soc., Chem. Commun. 1986, 1287-1288.
33. (b) Chackalamannil, S.; Wang, Y. Tetrahedron 1997, 53, 11203-11210.
34. 8. (a) Beak, P.; Koo Lee, W. J. Org. Chem. 1993, 55, 1109-1117.
35. (b) Comins, D. L.; Radi Benjelloun, N. Tetrahedron Lett. 1994, 35, 829-832.
36. 9. Oppolzer, W.; Bochet, C. G.; Merifield, E. Tetrahedron Lett. 1994, 35, 7015-7018.
37. 10. Nagasaka, T.; Hayashi, H.; Kumakawa, M.; Sakamoto, M.; Mizuno, M.; Hamaguchi, F. Heterocycles 1989, 29, 2157-2166. See also Refs. 2c and 5a.
38. 11. Wuts, P. G. M.; Jung, Y.-W. J. Org. Chem. 1988, 53, 1957-1965.
39. 12. Fuji, K.; Ichikawa, K.; Fujita, E. Chem. Pharm. Bull. 1979, 27, 3183-3185.
40. 13. (a) Takahata, H.; Inose, K.; Araya, N.; Momose, T. Heterocycles 1994, 38, 1961-1964.
41. (b) Solladié, G.; Huser, N. Recl. Trav. Chim. Pays-Bas 1995, 114, 153-156.
42. 14. Lupetidine [(2R,6R)-2,6-dimethylpiperidine] has also been synthesized following this method: Najdi, S.; Kurth, M. J. Tetrahedron Lett. 1990, 31, 3279-3282.
43. 15. See Refs. 2c, 4g, 4k, 5c, 5f, 5g, 7b, 8b, 9, 13a and 13b.
44. 16. Amat, M.; Llor, N.; Hidalgo, J.; Hernández, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977-980.
45. 17. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; p. 211.
46. 18. (a) Johnson, F. Chem. Rev. 1968, 68, 375-412.
47. (b) Hoffman, R. W. Chem. Rev. 1989, 89, 1841-1860.
48. 19. Cervinka, O. In The Chemistry of Enamines, Part I; Rappoport, Z., Ed. In The Chemistry of Functional Groups; Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1994; p. 489.
49. 20. (a) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904-3912.
50. (b) Denmark, S. E.; Edwards, J. P.; Nicaise, O. J. Org. Chem. 1993, 55, 569-578.
51. 21. Kantlehner, W. In Iminium Salts in Organic Chemistry; Böhme, H.; Viehe, H. G., Eds.; Wiley: New York, 1979; Part 2, p. 279.
52. 22. Gompper, R.; Elser, W. Org. Synth. 1968, 48, 97-101.
53. 23. For the alkylation of the α-position of cyclic amines via thioimidate salts with lithium acetylides, see: (a) Takahata, H.; Yamazaki, T. Heterocycles 1988, 27, 1953-1973.
54. (b) Takahata, H.; Takahashi, K.; Wang, E.-C.; Yamazaki, T. J. Chem. Soc., Perkin Trans. 1 1989, 1211-1214.
55. 24. Najdi, S.; Kurth, M. J. Tetrahedron Lett. 1990, 31, 3279-3282.
56. 25. (a) Kuzovkov, A. D.; Menshikov, G. P. Zhur. Obshchei Khim. 1950, 20, 1524 [Chem. Abstr. 1951, 45, 2485g].
57. (b) Hill, R. K.; Morgan, J. W. J. Org. Chem. 1966, 31, 3451-3452.
58. (c) Perrone, R.; Tortorella, V. Tetrahedron 1978, 34, 2533-2536.
59. 4c,d,k
60. 27. (a) 2-Alkyl: Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223-2226.
61. (b) 3-Alkyl: Amat, M.; Pshenichnyi, G.; Bosch, J.; Molins, E.; Miravitlles, C. Tetrahedron: Asymmetry 1996, 7, 3091-3094.
62. (c) cis-2,6-Dialkyl: see Ref. 16.
63. (d) trans-3,4-Dialkyl: Amat, M.; Hidalgo, J.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 1591-1594 and 1845. See also
64. (e) Amat, M.; Llor, N.; Bosch, J.; Solans, X. Tetrahedron 1997, 53, 719-730.
65. (f) Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J.; Molins, E.; Miravitlles, C. Tetrahedron: Asymmetry 1996, 7, 2501-2504.