Enantioselective total syntheses of slagenins A-C and their antipodes

Journal of Organic Chemistry

Volumn 68, Issue 6, 2003, Pages 2376-2384

  Jiang, Biao ^a   Liu, Jia Feng ^a   Zhao, Sheng Yin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIPODES;

CONDENSATION; KETONES; SYNTHESIS (CHEMICAL);

STEREOCHEMISTRY;

ALKALOID; SLAGENIN A; SLAGENIN B; SLAGENIN C; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHEMICAL ANALYSIS; CYCLIZATION; DRUG ISOLATION; ENANTIOSELECTIVITY; ENZYME ACTIVATION; HYDROGENATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; ANIMALS; COMBINATORIAL CHEMISTRY TECHNIQUES; FURANS; IMIDAZOLES; JAPAN; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; STEREOISOMERISM;

EID: 0037459684     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026773i     Document Type: Article

References (71)

1. For reviews, see: (a) Kobayashi, J.; Ishibashi, M. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: New York, 1992; Vol. 41, pp 41-124.
2. (b) Faulkner, D. J. Nat. Prod. Rep. 1999, 16, 155; 2002, 19, 1.
3. (b) Faulkner, D. J. Nat. Prod. Rep. 1999, 16, 155; 2002, 19, 1.
4. (a) Daninos-Zeghal, S.; Al Mourabit, A.; Ahond, A.; Poupat, C.; Potier, P. Tetrahedron 1997, 53, 7605.
5. (b) Anderson, G. T.; Chase, C. E.; Koh, Y.-h.; Stien, D.; Weinreb, S. M.; Shang, M. Y. J. Org. Chem. 1998, 63, 7594.
6. (c) Stein, D.; Anderson, G. T.; Chase, C. E.; Koh, Y.-h.; Weinreb, S. M. J. Am. Chem. Soc. 1999, 121, 9574.
7. (d) Namba, K.; Shinda, T.; Teramoto, T.; Ohfune, Y. J. Am. Chem. Soc. 2000, 122, 10708.
8. (e) Dilley, A. S.; Romo, D. Org. Lett. 2001, 3, 1535.
9. (f) Berree, F.; Bleis, P. G.; Carboni, B. Tetrahedron Lett. 2002, 43, 4935.
10. (a) Lindel, T.; Hoffmann, H. Tetrahedron Lett. 1997, 38, 8935.
11. (b) Lindel, T.; Hoffmann, H. Liebigs Ann./Recl. 1997, 1525.
12. (c) Lindel, T.; Hochgürtel, M. J. Org. Chem. 2000, 65, 2806.
13. (d) Jacquot, D. E. N.; Hoffmann, H.; Polborn, K.; Lindel, T. Tetrahedron Lett. 2002, 43, 3699.
14. (a) Xu, Y.-z.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 1996, 37, 8121.
15. (b) Xu, Y.-z.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 1997, 62, 456.
16. (c) Olofson, A.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 1997, 62, 7918.
17. (d) Olofson, A.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 1998, 63, 1248.
18. (e) Sosa, A. C. B.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 2000, 65, 610.
19. (f) Wiese, K. J.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 2002, 43, 5135.
20. Tsuda, M.; Uemoto, H.; Kobayashi, J. Tetrahedron Lett. 1999, 40, 5709.
21. Several bromopyrrole alkaloids have been isolated from marine sponge Agelas nakamurai: Uemoto, H.; Tsuda, M.; Kobayashi, J. J. Nat. Prod. 1999, 62, 1581.
22. Sosa, A. C. B.; Yakushijin, K.; Horne, D. A. Org. Lett. 2000, 2, 3443.
23. (a) For a later account of hypothetical biogenetic mechanism studies, see: Al Mourabit, A.; Potier, P. Eur. J. Org. Chem. 2001, 237.
24. (b) Kawasaki, I.; Sakaguchi, N.; Fukushima, N.; Fujioka, N.; Nikaido, F.; Yamashita, M.; Ohta, S. Tetrahedron Lett. 2002, 43, 4377.
25. For a preliminary account of enantioselective synthesis for the antipodes of slagenin B and C, see: Jiang, B.; Liu, J.-F.; Zhao, S. Y. Org. Lett. 2001, 3, 4011.
26. For a preliminary account of the enantioselective synthesis of slagenins A-C, see: (a) Jiang, B.; Liu, J.-F.; Zhao, S.-Y. Org. Lett. 2002, 4, 3951. (b) Gurjar, M. K.; Bera, S. Org. Lett. 2002, 4, 3569.
27. For a preliminary account of the enantioselective synthesis of slagenins A-C, see: (a) Jiang, B.; Liu, J.-F.; Zhao, S.-Y. Org. Lett. 2002, 4, 3951. (b) Gurjar, M. K.; Bera, S. Org. Lett. 2002, 4, 3569.
28. Avalos, M.; Babiano, R.; Cintas, P.; Jiménez, J. L.; Palacios, J. C.; Valencia, C. Tetrahedron 1993, 49, 2676.
29. (a) Vail, S. L.; Barker, R. H.; Mennitt, P. G. J. Org. Chem. 1965, 30, 2179.
30. (b) Gautam, S.; Katcham, R.; Nematollahi, J. Synth. Commun. 1979, 9, 863.
31. (c) Grillon, E.; Gallo, R.; Pierrot, M.; Boileau, J.; Wimmer, E. Tetrahedron Lett. 1988, 29, 1015.
32. Ihmels, H.; Maggini, M.; Prato, M.; Scorrano, G. Tetrahedron Lett. 1991, 32, 6215.
33. (a) Ager, D. J.; Laneman, S. A. Tetrahedron: Asymmetry 1997, 8, 3327.
34. (b) Davies, S. G.; Ichihara, O. Tetrahedron: Asymmetry 1996, 7, 1919.
35. (c) Yuasa, Y.; Tsuruta, H. Liebiegs Ann./Recl. 1997, 1877.
36. Jiang, B.; Chen, Z. Tetrahedron: Asymmetry 2001, 12, 2835.
37. Kobayashi, S.; Kobayashi, K.; Hirai, K. Synth. Lett. 1999, 909.
38. (a) Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
39. (b) Bull, J. R.; Dekoning, P. D. Eur. J. Org. Chem. 2001, 1189.
40. (c) Rainier, J. D.; Allcrein, S. P.; Cox, J. M. J. Org. Chem. 2001, 66, 1380.
41. Oxidation of diazoketone 8 with DMD generated in situ from oxone gave complex results.
42. Bromo-2-(trichloroacetyl)pyrrole was prepared from pyrrole following the reported procedures: (a) Kitamura, C.; Yamashita, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1443. (b) Bailey, D. M.; Johnson, R. E.; Albertson, N. F. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 618.
43. Bromo-2-(trichloroacetyl)pyrrole was prepared from pyrrole following the reported procedures: (a) Kitamura, C.; Yamashita, Y. J. Chem. Soc., Perkin Trans. 1 1997, 1443. (b) Bailey, D. M.; Johnson, R. E.; Albertson, N. F. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 618.
44. ORTEP figure and tables of X-ray crystallographic data for compound 10c can be found in the Supporting Information.
45. (a) Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. J. Am. Chem. Soc. 1987, 109, 2208. Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. 1988, 110, 4673.
46. (a) Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. J. Am. Chem. Soc. 1987, 109, 2208. Nicolaou, K. C.; Daines, R. A.; Uenishi, J.; Li, W. S.; Papahatjis, D. P.; Chakraborty, T. K. 1988, 110, 4673.
47. (b) For another report of the preparation of compound 14 from diacetone-L-glucose, see: Jones, M. F.; Noble, S. A.; Robertson, C. A.; Storer, R.; Highcock, R. M.; Lamont, R. B. J. Chem. Soc., Perkin Trans. 1 1992, 1427.
48. Baker, B. R.; Schaub, R. E. J. Am. Chem. Soc. 1955, 77, 5900.
49. Ma, T.; Pai, S. B.; Zhu, Y. L.; Lin, J. S.; Shanmuganathan, K.; Du, J.; Wang, C.; Kim, H.; Newton, M. G.; Cheng, Y. C.; Chu, C. K. J. Med. Chem. 1996, 39, 2835.
50. Gumina, G.; Schinazi, R. F.; Chu, C. K. Org. Lett. 2001, 3, 4177.
51. Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
52. Jacobson, K. A.; Siddiqi, S. M.; Olah, M. E.; Ji, X.-d.; Melman, N.; Bellamkonda, K.; Meshulam, Y.; Stiles, G. L.; Kim, H. O. J. Med. Chem. 1995, 38, 1720.
53. A preparation of the antipode of compound 15 from glucose was reported: Bentley, N.; Dowdeswell, C. S.; Singh, G. Heterocycles 1995, 41, 2499.
54. (a) Huang, B.-G.; Bobek, M. Carbohydr. Res. 1998, 308, 319.
55. (b) Lu, D.-M.; Min, J.-M.; Zhang, L.-H. Carbohydr. Res. 1998, 317, 193.
56. (a) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
57. (b) Gurjar, M. K.; Ravindranadh, S. V.; Kumar, P. Chem. Commun. 2001, 917.
58. (c) Li, N.-S.; Tang, X.-Q.; Piccirilli, J. A. Org. Lett. 2001, 3, 1025.
59. (d) Cook, G. P.; Greenberg, M. M. J. Org. Chem. 1994, 59, 4704.
60. Experimental details and characterization may be found in the Supporting Information.
61. (a) Corey, E. J.; Bock, M. G. Tetrahedron Lett. 1975, 2643.
62. (b) Prato, M.; Quinity, U.; Scorrano, G.; Sturaro, A. Synthesis 1982, 679.
63. (c) Juaristi, E.; Tapia, J.; Mendez, R. Tetrahedron 1986, 42, 1253.
64. (d) Cossy, J. Synthesis 1987, 1113.
65. Wittig, G.; Schöllkopf, U. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 751.
66. Akashi, K.; Palermo, R. E.; Sharpless, K. B. J. Org. Chem. 1978, 43, 2063.
67. (a) Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
68. (b) Amon, C. M.; Banwell, M, G.; Gravatt, G. L. J. Org. Chem. 1987, 52, 4851.
69. (c) Ireland, R. E.; Norbeck, D. W. J. Org. Chem. 1985, 50, 2198.
70. (d) Newman, M. S.; Davis, C. C. J. Org. Chem. 1967, 32, 66.
71. Tius, M. A.; Fauq, A. H. J. Am. Chem. Soc. 1986, 108, 1035.