A general asymmetric route for the synthesis of the alexine and australine family of pyrrolizidine alkaloids. The first asymmetric synthesis of 1,2-diepi-alexine and 1,2,7-triepi-australine

Tetrahedron Letters

Volumn 46, Issue 51, 2005, Pages 8865-8868

  Chikkanna, Dinesh ^a   Singh, Om V ^a   Kong, Suk Bin ^a,b   Han, Hyunsoo ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

^b UNIVERSITY OF THE INCARNATE WORD   (United States)

Author keywords

Double cyclization; Epoxidation; Olefin cross metathesis; Pyrrolizidine alkaloids; Regioselective asymmetric aminohydroxylation

Indexed keywords

1,2 DIEPIALEXINE; 1,2,7 TRIEPIAUSTRALINE; ALDEHYDE; ALKENE; EPOXIDE; MAGNESIUM DERIVATIVE; PYRROLIZIDINE ALKALOID; UNCLASSIFIED DRUG; VINYLMAGNESIUM BROMIDE;

AMINOHYDROXYLATION; ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLIZATION; DIASTEREOISOMER; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 27944454053     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.074     Document Type: Article

References (76)

1. For alexine, R.J. Nash, L.E. Fellows, J.V. Dring, G.W.J. Fleet, A.E. Derome, T.A. Hamor, A.M. Scofield, and D.J. Watkin Tetrahedron Lett. 29 1988 2487 2490
2. A.M. Scofield, J.T. Rossiter, P. Witham, G.C. Kite, R.J. Nash, and L.E. Fellows Phyrochemistry 29 1990 107 109
3. For australine, R.J. Molyneux, M. Benson, R.Y. Wong, J.E. tropea, and A.D. Elbein J. Nat. Prod. 51 1988 1198 1206
4. B.L. Rhinehart, K.M. Robinson, A.J. Payne, M.E. Wheatly, J.L. Fisher, P.S. Liu, and W. Cheng Life Sci. 41 1987 2325 2331
5. P.B. Anzeveno, L.J. Creemer, J.K. Daniel, C.H.R. King, and P.S. Liu J. Org. Chem. 54 1989 2539 2542
6. P.S. Johnson, H.E. Lebovitz, R.F. Coniff, D.C. Simonson, P. Raskin, and C.L. Munera J. Clin. Endocrinol. Metab. 83 1998 1515 1522
7. G.K. Ostrander, N.K. Scribner, and L.R. Rohrschneider Cancer Res. 48 1988 1091 1094
8. Bitonti, A. J.; Sjoersma, A.; McCann, P. P. Eur. Patent App. EP 423.728 1991, 14 pp.
9. G.W.J. Fleet, A. Karpas, R.A. Dwek, L.E. Fellows, A.S. Tyms, S. Peturrson, S.K. Namgoong, N.G. Ramsden, P.W. Smith, J.C. Son, F. Wilson, D.R. Witty, G.S. Jacob, and T.W. Rademacher FEBS Lett. 237 1988 128 132
10. R.A. Gruters, J.J. Neefjes, M. Tersmette, R.E.Y. de Goede, A. Tulp, H.G. Huisman, F. Miedema, and H.L. Ploegh Nature 330 1987 74 77
11. A.E. Stutz Iminosugars as Glycosidase Inhibitors. Nojirimycin and Beyond 1999 Wiley-VCH Weinheim, Germany
12. O.R. Martin Y. Chapleur Carbohydrate Mimics. Concepts and Methods 1998 Wiley-VCH Weinheim, Germany
13. N. Asano, R.J. Nash, R.J. Molyneux, and G.W.J. Fleet Tetrahedron: Asymmetry 11 2000 1645 1680
14. R.J. Molyneux, Y.T. Pan, J.E. Tropea, M. Benson, G.P. Kaushal, and A.D. Elbein Biochemistry 30 1991 9981 9987
15. R.J. Nash, L.E. Fellows, J.V. Dring, G.W.J. Fleet, A. Girdhar, N.G. Ramsden, J.M. Peach, M.P. Hegarty, and A.M. Scofield Phytochemistry 29 1990 111 114
16. J.E. Tropea, R.J. Molyneux, G.P. Kaushal, Y.T. Pan, M. Mitchell, and A.D. Elbein Biochemistry 28 1989 2027 2034
17. C.M. Harris, T.M. Harris, R.J. Molyneux, J.E. Tropea, and A.D. Elbein Tetrahedron Lett. 30 1989 5685 5688
18. R.J. Nash, L.E. Fellows, A.C. Plant, G.W.J. Fleet, A.E. Derome, P.D. Baird, M.P. Hegarty, and A.M. Scofield Tetrahedron 44 1988 5959 5964
19. T.J. Donohoe, and H.O. Sintim Org. Lett. 6 2004 2003 2006
20. M. Tang, and S. Pyne J. Org. Chem. 68 2003 7818 7824
21. J.K. Gallos, V.C. Sarli, C.I. Stathakis, T.V. Koftis, V.R. Nachmia, and E. Coutouli-Argyropoulou Tetrahedron 58 2002 9351 9357
22. J.-B. Behr, A. Erard, and G. Guillerm Eur. J. Org. Chem. 2002 1256 1262
23. J.D. White, and P. Hrnciar J. Org. Chem. 65 2000 9129 9142
24. W.H. Pearson, and J.V. Hines J. Org. Chem. 65 2000 5785 5793
25. H. Yoda, F. Asai, and K. Takabe Synlett 2000 1001 1003
26. H. Yoda, H. Katoh, and K. Takabe Tetrahedron Lett. 41 2000 7661 7665
27. G. Rassu, P. Carta, L. Pinna, L. Battistini, F. Zanardi, D. Acquotti, and G. Casiraghi Eur. J. Org. Chem. 1999 1395 1400
28. M.R. Wormald, R.J. Nash, P. Hrnciar, J.D. White, R.J. Molyneux, and G.W.J. Fleet Tetrahedron: Asymmetry 9 1998 2549 2558
29. N. Ikota, H. Nakagawa, S. Ohno, K. Noguchi, and K. Okuyama Tetrahedron 54 1998 8985 8998
30. A. Hall, K.P. Meldrum, P.R. Therond, and R.H. Wightman Synlett 1997 123 125
31. R.H. Furneaux, G.J. Gainsford, J.M. Mason, and P.C. Tyler Tetrahedron 50 1994 2131 2160
32. N. Ikota Tetrahedron Lett. 33 1992 2553 2556
33. S. Choi, I. Bruce, A.J. Fairbanks, G.W. Fleet, A.H. Jones, R.J. Nash, and L.E. Fellows Tetrahedron Lett. 32 1991 5517 5520
34. G.W.J. Fleet, M. Haraldsson, R.J. Nash, and L.E. Fellows Tetrahedron Lett. 29 1988 5441 5444
35. D.L. Taylor, R. Nash, L.E. Fellows, M.S. Kang, and A.S. Tyms Antiviral Chem. Chemother. 3 1992 273 277
36. Elbein, A. D.; Tropea, J. E.; Molyneux, R. J. U.S. Pat. Appl. US 289907.
37. Chem. Abstr. 113 1990 P91444p
38. Fellows, L.; Nash, R. PCT Int. Appl. WO GB Appl. 89/7951
39. Chem. Abstr. 114 1990 143777f
40. For reviews, see: J.R. Liddell Nat. Prod. Rep. 16 1999 499 507
41. G. Casiraghi, F. Zanardi, G. Rassu, and L. Pinna Org. Prep. Proced. Int. 28 1996 641 682
42. For individual synthesis, see Refs. 8, 11, and 12.
43. S.E. Denmark, and J.J. Cottell J. Org. Chem. 66 2001 4276 4284
44. S.E. Denmark, and B. Herbert J. Org. Chem. 65 2000 2887 2896
45. S.E. Denmark, and E.A. Martinborough J. Am. Chem. Soc. 121 1999 3046 3056
46. A. Romero, and C.-H. Wong J. Org. Chem. 65 2000 8264 8268
47. For a review, see: T. Katsuki E.N. Jacobsen A. Pfaltz H. Yamamoto Comprehensive Asymmetric Catalysis I-III Vol. II 1999 Springer Berlin 621
48. For reviews, see: A. Vernall, and A.D. Abell Aldrichim. Acta 36 2003 93 105
49. F.D. Toste, A.K. Chatterjee, and R.H. Grubbs Pure Appl. Chem. 74 2002 7 10
50. R. Roy, and S.K. Das Chem. Commun. 2000 519 529
51. A. Chatterjee, T.-L. Choi, D.P. Sanders, and R.H. Grubbs J. Am. Chem. Soc. 125 2003 11360 11370 and references cited therein
52. H. Han, C.W. Cho, and K.D. Janda Chem. Eur. J. 5 1999 1565 1569
53. O.V. Singh, and H. Han Tetrahedron Lett. 44 2003 2387 2391
54. O.V. Singh, and H. Han Tetrahedron Lett. 44 2003 5289 5292
55. For other approaches, see: A.J. Morgan, C.E. Masse, and J.S. Panek Org. Lett. 1 1999 1949 1952
56. C.-C. Chuang, V. Vassar, Z. Ma, R. Geney, and I. Ojima Chirality 14 2002 151 162
57. B. Tao, G. Schlingloff, and K.B. Sharpless Tetrahedron Lett. 39 1998 2507 2510
58. R. Angelaud, Y. Landais, and K. Schenk Tetrahedron Lett. 38 1997 1407 1410
59. T.J. Donohoe, P.D. Johnson, R.J. Pye, and M. Keenan Org. Lett. 6 2004 2583 2585 and references cited therein
60. For the development of the AA reaction, see: G. Li, H.-T. Chang, and K.B. Sharpless Angew. Chem., Int. Ed. Engl. 35 1996 451 454
61. J. Rudolph, P.C. Sennhenn, C.P. Vlaar, and K.B. Sharpless Angew. Chem., Int. Ed. Engl. 35 1996 2810 2813
62. M. Bruncko, G. Schlingloff, and K.B. Sharpless Angew. Chem., Int. Ed. 36 1997 1483 1486
63. M.A. Andersson, R. Epple, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 472 475 and references cited therein
64. For the recent reviews on the AA reaction, see: K. Muniz Chem. Soc. Rev. 33 2004 166 174
65. J.A. Bodkin, and M.D. McLeod J. Chem. Soc., Perkin Trans. 1 2002 2733 2746
66. O. Reiser Angew. Chem., Int. Ed. Engl. 35 1996 1308 1309
67. For a recent review on other methodologies for the stereoselective synthesis of vicinal amino alcohols, see: S.C. Bergmeier Tetrahedron 56 2000 2561 2576
68. H. Takaku, K. Kamaike, and H. Tsuchiya J. Org. Chem. 49 1984 51 56
69. M.J. Burk, and J.G. Allen J. Org. Chem. 62 1997 7054 7057
70. A. Dondoni, D. Perrone, and P. Merino J. Org. Chem. 60 1995 8074 8080
71. For a review, see: C. Bolm Coord. Chem. Rev. 237 2003 245 256
72. S. Singh, and H. Han Tetrahedron Lett. 45 2004 6349 6352
73. Y. Hoshino, and H. Yamamoto J. Am. Chem. Soc. 122 2000 10452 10453
74. C. Bolm, and T. Kuhn Synlett 2000 899 901
75. T. Fukuyama, A.A. Laird, and L.M. Hotchkiss Tetrahedron Lett. 26 1985 6291 6292
76. 2O): δ 80.7, 79.3, 75.6, 72.7, 71.6, 59.8, 54.7, 36.3.