Nonchiral-pool synthesis of (+)-hyacinthacine B1

Synlett

Volumn , Issue 7, 2009, Pages 1141-1143

  Reddy, Paidi Venkatram ^a   Koos, Peter ^a   Veyron, Amaël ^a   Greene, Andrew E ^a   Delair, Philippe ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Azasugars; Cycloadditions; Double Tamao Fleming oxidation; Natural products; Stereoselective synthesis

Indexed keywords

HYACINTHACINE B1; IMINOSUGAR; PYRROLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 67649418044     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088147     Document Type: Article

References (64)

1. Iminosugars; Compain, P.; Martin, O. R., Eds.; John Wiley and Sons: Chichester, 2007.
2. (a) Asano, N.; Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymmetry 2000, 11, 1645.
3. (b) Butters, T. D.; Dwek, R. A.; Platt, F. M. Chem. Rev. 2000, 100, 4683.
4. (c) Robina, I.; Moreno-Vargas, A. J.; Carmona, A. T.; Vogel, P. Curr. Drug Metab. 2004, 5, 329.
5. (d) Borges de Melo, E.; da Silva Gomes, A.; Carvalho, I. Tetrahedron 2006, 62, 10277.
6. (e) Gerber-Lemaire, S.; Juillerat- Jeanneret, L. Mini Rev. Med. Chem. 2006, 6, 1043.
7. For a review on polyhydroxylated pyrrolizidines, see: (a) Yoda, H. Curr. Org. Chem. 2002, 6, 223.
8. For a review on pyrrolizidines, see: (b) Liddell, J. R. Nat. Prod. Rep. 2002, 19, 773.
9. (c) Liddell, J. R. Nat. Prod. Rep. 2001, 18, 441.
10. (d) Liddell, J. R. Nat. Prod. Rep. 2000, 17, 455.
11. (e) Liddell, J. R. Nat. Prod. Rep. 1999, 16, 499.
12. (f) Liddell, J. R. Nat. Prod. Rep. 1998, 15, 363.
13. (g) Nash, R. J.; Watson, A. A.; Asano, N. In Alkaloids: Chemical & Biological Perspectives, Vol.11; Pelletier, S. W., Ed.; Elsevier Science: Oxford, 1996, 345.
14. See: Kato, A.; Kato, N.; Adachi, I.; Hollinshead, J.; Fleet, G. W.; Kuriyama, C.; Ikeda, K.; Asano, N.; Nash, R. J. J. Nat. Prod. 2007, 70, 993; and references cited therein.
15. For recent examples, see: (a) Chabaud, L.; Landais, Y.; Renaud, P. Org. Lett. 2005, 7, 2587.
16. (b) Desvergenes, S.; Py, S.; Vallée, Y. J. Org. Chem. 2005, 70, 1459.
17. (c) Donohoe, T. J.; Sintim, H. O.; Hollinshead, J. J. Org. Chem. 2005, 70, 7297.
18. (d) Dewi-Wülfing, P.; Blechert, S. Eur. J. Org. Chem. 2006, 1852.
19. (e) Donohoe, T. J.; Thomas, R. E. Chem. Rec. 2007, 7, 180.
20. (f) Zhou, L.; Chen, J.; Cao, X.-P. Synthesis 2007, 1359.
21. (g) Izquierdo, I.; Plaza, M. T.; Tamayo, J. A.; Sanchez-Cantalejo, F. Eur. J. Org. Chem. 2007, 6078.
22. (h) Izquierdo, I.; Plaza, M. T.; Tamayo, J. A.; Yanez, V.; Lo Re, D.; Sanchez-Cantalejo, F. Tetrahedron 2008, 64, 4613.
23. (i) Donohoe, T. J.; Thomas, R. E.; Cheeseman, M. D.; Rigby, C. L.; Bhalay, G.; Linney, I. D. Org. Lett. 2008, 10, 3615.
24. (j) Chandrasekhar, S.; Parida, B. B.; Rambabu, C. J. Org. Chem. 2008, 73, 7826.
25. (k) For asymmetric syntheses of related compounds, see: Denmark, S. E.; Martinborough, E. A. J. Am. Chem. Soc. 1999, 121, 3046 (australine).
26. (l) Trost, B. M.; Aponick, A.; Stanzl, B. N. Chem. Eur. J. 2007, 13, 9547 (australine).
27. (m) Denmark, S. E.; Hurd, A. R. J. Org. Chem. 2000, 65, 2875 (casuarine).
28. Reddy, P. V.; Veyron, A.; Koos, P.; Bayle, A.; Greene, A. E.; Delair, P. Org. Biomol. Chem. 2008, 6, 1170.
29. Greene, A. E.; Charbonnier, F. Tetrahedron Lett. 1985, 26, 5525.
30. Pyrrolidines: (a) Kanazawa, A.; Gillet, S.; Delair, P.; Greene, A. E. J. Org. Chem. 1998, 63, 4660.
31. (b) Delair, P.; Brot, E.; Kanazawa, A.; Greene, A. E. J. Org. Chem. 1999, 64, 1383.
32. (c) Ceccon, J.; Poisson, J.-F.; Greene, A. E. Synlett 2005, 1413.
33. Indolizidines: (a) Pourashraf, M.; Delair, P.; Rasmussen, M.; Greene, A. E. J. Org. Chem. 2000, 65, 6966.
34. (b) Rasmussen, M.; Delair, P.; Greene, A. E. J. Org. Chem. 2001, 66, 5438.
35. (c) Ceccon, J.; Poisson, J.-F.; Greene, A. E. Org. Lett. 2006, 8, 4739.
36. Pyrrolizidines: (a) Roche, C.; Delair, P.; Greene, A. E. Org. Lett. 2003, 5, 1741.
37. (b) Roche, C.; Kadlecíková, K.; Veyron, A.; Delair, P.; Philouze, C.; Greene, A. E.; Flot, D.; Burghammer, M. J. Org. Chem. 2005, 70, 8352.
38. Kato, A.; Adachi, I.; Miyauchi, M.; Ikeda, K.; Komae, T.; Kizu, H.; Kameda, Y.; Watson, A. A.; Nash, R. J.; Wormald, M. R.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 1999, 316, 95.
39. 1 starting from L-pyroglutamic acid has been published prior to this report. See: Sengoku, T.; Satoh, Y.; Oshima, M.; Takahashi, M.; Yoda, H. Tetrahedron 2008, 64, 8052.
40. 1.
41. 1H NMR) mixture of diastereomers. The minor enantiomer filtered out over the remainder of the synthesis.
42. (a) Bruylants, P. Bull. Soc. Chim. Belg. 1924, 33, 467.
43. For mechanistic studies, see: (b) Beaufort-Droal, V.; Pereira, E.; Théry, V.; Aitken, D. J. Tetrahedron 2006, 62, 11948.
44. (c) Aitken, D. J.; Beaufort, V.; Chalard, P.; Cladière, J. L.; Dufour, M.; Pereira, E.; Théry, V. Tetrahedron 2002, 58, 5933.
45. For a review, see: (a) Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359.
46. See also: (b) Husson, H. P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383.
47. (a) Durand, J.-O.; Larchevêque, M.; Petit, Y. Tetrahedron Lett. 1998, 39, 5743.
48. (b) Matsubara, R.; Kawai, N.; Kobayashi, S. Angew. Chem. Int. Ed. 2006, 45, 3814.
49. (a) Xia, Q.; Ganem, B. Tetrahedron. Lett. 2002, 43, 1597.
50. (b) White, J. M.; Tunoori, A. R.; Georg, G. I. J. Am. Chem. Soc. 2000, 122, 11995.
51. Kim, S.; Ahn, K. H. J. Org. Chem. 1984, 49, 1717.
52. For a review, see: Jones, G. R.; Landais, Y. Tetrahedron 1996, 52, 7599.
53. See, for example: (a) Smitrovich, J. H.; Woerpel, K. A. J. Org. Chem. 1996, 61, 6044.
54. (b) Molander, G. A.; Nichols, P. J. J. Org. Chem. 1996, 61, 6040.
55. (c) Overman, L. O.; Wild, H. Tetrahedron Lett. 1989, 30, 647.
56. (d) Polniaszek, R. P.; Dillard, L. W. J. Org. Chem. 1992, 57, 4103. See also ref. 22g
57. (a) Fleming, I.; Ghosh, S. K. J. Chem. Soc., Chem. Commun. 1992, 1775.
58. (b) Chen, R. M.; Weng, W. W.; Luh, T. Y. J. Org. Chem. 1995, 60, 3272.
59. (c) Shimada, T.; Mukaide, K.; Shinohara, A.; Han, J. W.; Hayashi, T. J. Am. Chem. Soc. 2002, 124, 1584.
60. (d) Berry, M. B.; Griffiths, R. J.; Sanganee, M. J.; Steel, P. G.; Whelligan, D. K. Tetrahedron Lett. 2003, 44, 9135.
61. (e) Landais, Y.; Mahieux, C. Tetrahedron Lett. 2005, 46, 675.
62. (f) Restorp, P.; Fischer, A.; Somfai, P. J. Am. Chem. Soc. 2006, 128, 12646.
63. (g) Dressel, M.; Restorp, P.; Somfai, P. Chem. Eur. J. 2008, 14, 3072; and references cited therein.
64. 13C NMR.