Prolinamide/PPTS-catalyzed Hajos-Parrish annulation: Efficient approach to the tricyclic core of cylindricine-type alkaloids

Synlett

Volumn , Issue 18, 2008, Pages 2831-2835

  Zhang, Xiao Ming ^a   Wang, Min ^a   Tu, Yong Qiang ^a   Fan, Chun An ^a   Jiang, Yi Jun ^a   Zhang, Shu Yu ^a   Zhang, Fu Min ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Cylindricine type alkaloids; Hajos Parrish annulation; Intramolecular schmidt reaction; Prolinamide; Wieland Miescher ketone analogues

Indexed keywords

ALKALOID DERIVATIVE; KETONE DERIVATIVE; PROLINE DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; HYDROBORATION; HYDROGENATION; SYNTHESIS; X RAY ANALYSIS;

EID: 56849120391     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083542     Document Type: Article

References (66)

1. For recent instance, see: (a) Kaliappan, K. P.; Ravikumar, V. Org. Lett. 2007, 9, 2417.
2. (b) Lanfranchi, D. A.; Hanquet, G. J. Org. Chem. 2006, 71, 4854.
3. (c) González, S. A.; Bradshaw, B. J.; Bonjoch, C. J. J. Org. Chem. 2005, 70, 3749.
4. (d) Hagiwara, H.; Hamano, K.; Nozawa, M.; Hoshi, T.; Suzuki, T.; Kido, F. J. Org. Chem. 2005, 70, 2250.
5. (e) Shigehisa, H.; Mizutani, T.; Tosaki, S.; Ohshima, T.; Shibasaki, M. Tetrahedron 2005, 61, 5057.
6. (f) Kanoh, N.; Smith, A. B. I. I. I.; Ishiyama, H.; Minakawa, N.; Rainier, J. D.; Hartz, R. A.; Cho, Y. S.; Cui, H.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 8228.
7. (g) Suzuki, A.; Nakatani, M.; Nakamura, M.; Kawaguchi, K.; Inoue, M.; Katoh, T. Synlett 2003, 329.
8. (h) Deng, W.-P.; Zhong, M.; Guo, X.-C.; Kende, A. S. J. Org. Chem. 2003, 68, 7422.
9. (i) Ling, T.; Chowdhury, C.; Kramer, B. A.; Vong, B. G.; Palladino, M. A.; Theodorakis, E. A. J. Org. Chem. 2001, 66, 8843.
10. (a) Wieland, P.; Miescher, K. Helv. Chim. Acta 1950, 33, 2215.
11. (b) Hajos, Z. G.; Parrish, D. R. J. Org. Chem. 1974, 39, 1615.
12. (c) Eder, U.; Sauer, G.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1971, 10, 496.
13. (a) Davies, S. G.; Russell, A. J.; Sheppard, R. L.; Smith, A. D.; Thomson, J. E. Org. Biomol. Chem. 2007, 5, 3190.
14. (b) He, L. Hecheng Huaxue 2007, 15, 231.
15. (c) Sulzer-Mossé, S.; Laars, M.; Kriis, K.; Kanger, T.; Alexakis, A. Synthesis 2007, 1729.
16. (d) Kanger, T.; Kriis, K.; Laars, M.; Kailas, T.; Müürisepp, A.-M.; Pehk, T.; Lopp, M. J. Org. Chem. 2007, 72, 5168.
17. (e) Lacoste, E.; Vaique, E.; Berlande, M.; Pianet, I.; Vincent, J.-M.; Landais, Y. Eur. J. Org. Chem. 2007, 167.
18. (f) Nagamine, T.; Inomata, K.; Endo, Y.; Paquette, L. A. J. Org. Chem. 2007, 72, 123.
19. (g) Kriis, K.; Kanger, T.; Laars, M.; Kailas, T.; Müürisepp, A.-M.; Pehk, T.; Lopp, M. Synlett 2006, 1699.
20. (h) Kasai, Y.; Shimanuki, K.; Kuwahara, S.; Watanabe, M.; Harada, N. Chirality 2006, 18, 177.
21. (i) Davies, S. G.; Sheppard, R. L.; Smith, A. D.; Thomson, J. E. Chem. Commun. 2005, 3802.
22. (j) Cheong, P. H.; Houk, K. N.; Warrier, J. S.; Hanessian, S. Adv. Synth. Catal. 2004, 346, 1111.
23. (k) Fuhshuku, K.-I.; Tomita, M.; Sugai, T. Adv. Synth. Catal. 2003, 345, 766.
24. (l) Lo, L.-C.; Shie, J.-J.; Chou, T.-C. J. Org. Chem. 2002, 67, 282.
25. (m) Hioki, H.; Hashimoto, T.; Kodama, M. Tetrahedron: Asymmetry 2000, 11, 829.
26. (n) Fuhshuku, K.-I.; Funa, N.; Akeboshi, T.; Ohta, H.; Hosomi, H.; Ohba, S.; Sugai, T. J. Org. Chem. 2000, 65, 129.
27. (o) Bui, T.; Barbas, C. F. Tetrahedron Lett. 2000, 41, 6951.
28. Gu, P.; Zhao, Y.-M.; Tu, Y. Q.; Ma, Y.; Zhang, F. Org. Lett. 2006, 8, 5271.
29. (a) Hiroya, K.; Takahashi, T.; Shimomae, K.; Sakamoto, T. Chem. Pharm. Bull. 2005, 53, 207.
30. (b) Ziegler, F. E.; Wallace, O. B. J. Org. Chem. 1995, 60, 3626.
31. Ramachary, D. B.; Kishor, M. J. Org. Chem. 2007, 72, 5056.
32. (a) Inomata, K.; Barrague, M.; Paquette, L. A. J. Org. Chem. 2005, 70, 533.
33. (b) Hanselmann, R.; Benn, M. Synth. Commun. 1996, 26, 945.
34. For very recent instance of prolinamide catalytic aldol reaction, see: (a) Guillena, G.; Hita, M.; Nájera, C.; Viózquez, S. F. Tetrahedron: Asymmetry 2007, 18, 2300.
35. (b) Russo, A.; Botta, G.; Lattanzi, A. Tetrahedron 2007, 63, 11886.
36. (c) Tang, Z.; Marx, A. Angew. Chem. Int. Ed. 2007, 46, 7297.
37. (d) Hong, B.; Wu, M.; Tseng, H.; Huang, G.; Su, C.; Liao, J. J. Org. Chem. 2007, 72, 8459.
38. (e) Peng, Y.; Liu, H.; Cui, M.; Cheng, J. Chin. J. Chem. 2007, 25, 962.
39. (f) Dodda, R.; Zhao, C. Synlett 2007, 1605.
40. (g) Guillena, G.; Hita, M. C.; Nájera, C. Tetrahedron: Asymmetry 2007, 18, 1272.
41. (h) Aratake, S.; Itoh, T.; Okano, T.; Usui, T.; Shoji, M.; Hayashi, Y. Chem. Commun. 2007, 2524.
42. (i) Zhang, F.; Peng, Y.; Liao, S.; Gong, Y. Tetrahedron 2007, 63, 4636.
43. (j) Ma, G.; Zhang, Y.; Shi, M. Synthesis 2007, 197.
44. Hayashi, Y.; Yamaguchi, J.; Hibino, K.; Sumiya, T.; Urushima, T.; Shoji, M.; Hashizume, D.; Koshino, H. Adv. Synth. Catal. 2004, 346, 1435.
45. (a) Tang, Z.; Cun, L.-F.; Cui, X.; Mi, A.-Q.; Jiang, Y.-Z.; Gong, L.-Z. Org. Lett. 2006, 8, 1263.
46. (b) Cobb, A. J. A.; Shaw, D. M.; Longbottom, D. A.; Gold, J. B.; Ley, S. V. Org. Biomol. Chem. 2005, 3, 84.
47. (c) Berkessel, A.; Koch, B.; Lex, J. Adv. Synth. Catal. 2004, 346, 1141.
48. Rajamannar, T.; Balasubramanian, K. K. Synth. Commun. 1994, 24, 279.
49. (a) Blackman, A. J.; Li, C.; Hockless, D. C. R.; Skelton, B. W.; White, A. H. Tetrahedron 1993, 49, 8645.
50. (b) Li, C.; Blackman, A. J. Aust. J. Chem. 1994, 47, 1355.
51. (c) Li, C.; Blackman, A. J. Aust. J. Chem. 1995, 48, 955.
52. (a) Biard, J. F.; Guyot, S.; Roussakis, C.; Verbist, J. F.; Vercauteren, J.; Weber, J. F.; Boukef, K. Tetrahedron Lett. 1994, 35, 2691.
53. (b) Juge, M.; Grimaud, N.; Biard, J. F.; Sauviat, M. P.; Nabil, M.; Verbist, J. F.; Petit, J. Y. Toxicon 2001, 39, 1231.
54. (c) Sauviat, M. P.; Vercauteren, J.; Grimaud, N.; Juge, M.; Nabil, M.; Petit, J. Y.; Biard, J. F. J. Nat. Prod. 2006, 69, 558.
55. For a review and some recent work on the total synthesis of cylindricines and lepadiformine, see: (a) Weinreb, S. M. Chem. Rev. 2006, 106, 2531.
56. (b) Caldwell, J. J.; Craig, D. Angew. Chem. Int. Ed. 2007, 119, 2685.
57. (c) Flick, A. C.; Caballero, M. J. A.; Padwa, A. Org. Lett. 2008, 10, 1871.
58. (a) Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965.
59. (b) Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449.
60. (c) Iyengar, R.; Schildknegt, K.; Aubé, J. Org. Lett. 2000, 2, 1625.
61. 2O-AcOH (100:1.5) as the solvent and 2 equiv of MVK under reflux conditions in the second step.
62. (a) Kabalka, G. W.; Yu, S.; Li, N. S. Tetrahedron Lett. 1997, 38, 5455.
63. (b) Kabalka, G. W.; Yu, S.; Li, N. S. Can. J. Chem. 1998, 76, 800.
64. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley: New York, 1999, Chap. 4.
65. Thomsen, I.; Clausen, K.; Scheibye, S.; Lawesson, S.-O. Org. Synth. 1984, 62, 158.
66. CCDC 696349 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.