A formal synthesis of thymine polyoxin C

Tetrahedron Asymmetry

Volumn 16, Issue 10, 2005, Pages 1845-1854

  Harding, Kenn E ^a   Southard, Jack M ^b  

^a TEXAS A AND M UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT BROWNSVILLE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; BENZYL DERIVATIVE; FURAN DERIVATIVE; THYMINE POLYOXIN C;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 19444378238     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.03.034     Document Type: Article

References (71)

1. K. Isono, and S. Suzuki Agric. Biol. Chem. 29 1965 848 854
2. K. Isono, S. Suzuki, J. Nagatsu, Y. Kawashima, K. Yamagata, K. Sasaki, and K. Hashimoto Agric. Biol. Chem. 30 1966 817 819
3. K. Isono, S. Suzuki, K. Sasaki, and K. Kobinata Agric. Biol. Chem. 31 1967 190 199
4. K. Isono, K. Kobinata, and S. Suzuki Agric. Biol. Chem. 32 1968 792 793
5. K. Isono, S. Suzuki, M. Tanaka, T. Nanbata, and K. Shibuya Tetrahedron Lett. 26 1970 425 428
6. K. Isono, and S. Suzuki Heterocycles 13 1979 333 351
7. K. Isono Antibiotics 41 1988 1711
8. N. Mita, O. Tamura, H. Ishibashi, and M. Sakamoto Org. Lett. 4 2002 1111 1114
9. S. Merino, S. Franco, F.L. Merchan, and T. Tejero J. Org. Chem. 65 2000 5575 5589
10. A. Chen, E.J. Thomas, and P.D. Wilson J. Chem. Soc., Perkin Trans. 1 1999 3305
11. A.K. Ghosh, and Y. Wang J. Org. Chem. 64 1999 2789
12. A.K. Ghosh, and Y. Wang J. Org. Chem. 63 1998 6735
13. A. Dondoni, F. Franaco, F. Junquera, F.L. Merchan, P. Merino, and T. Tejero J. Org. Chem. 62 1997 5497
14. N.S. Simpkins, and D.M. Gethin Tetrahedron 42 1997 14417 14436
15. B.M. Trost, and Z. Shi J. Am. Chem. Soc. 118 1996 3037 3038
16. G. Guillerm, and C.M. Evina Tetrahedron Lett. 37 1996 163 166
17. A. Dondoni, F. Junquera, F.L. Merchán, P. Merino, and T. Tejero Tetrahedron Lett. 35 1994 9439 9442
18. N. Chida, K. Koizumi, Y. Kitada, C. Yokahama, and S. Ogawa J. Chem. Soc., Chem. Commun. 1994 111 113
19. E.J. Thomas, A. Chen, I. Savage, and P.D. Wilson Tetrahedron Lett. 42 1993 6769 6772
20. P. Vogel, and Y. Auberson Tetrahedron 46 1990 7019 7032
21. P. Garner, and J.-M. Park J. Org. Chem. 55 1990 3772 3787
22. A.G.M. Barrett, and S.A. Lebold J. Org. Chem. 55 1990 3853 3857
23. P. Garner, and J.-M. Park Tetrahedron Lett. 30 1989 5065 5068
24. T. Mukaiyama, K. Suzuki, T. Yamada, and F. Tabusa Tetrahedron 46 1990 265 276
25. H. Ohrui, H. Kuzuhara, and S. Emoto Tetrahedron Lett. 12 1971 4267 4270
26. J.G. Moffatt, N.P. Damodaran, and G.H. Jones J. Am. Chem. Soc. 93 1971 3812 3813
27. M. Nishimura, T. Naka, and T. Hashizume Tetrahedron Lett. 12 1971 95 98
28. H. Vorbrüggen, K. Krolikkiewicz, and B. Bennua Chem. Ber. 114 1981 1234
29. H. Vorbrüggen, and U. Niedballa J. Org. Chem. 39 1974 3654 3674
30. T. Nishimura, and I. Iwai Chem. Pharm. Bull. 12 1964 352 356
31. J.-A. Nasman, and K.G. Pensar Synthesis 1985 786 787
32. B. Figadere, J.F. Peyrat, and A. Cave J. Org. Chem. 62 1997 3428 3429
33. K.E. Harding, M.T. Coleman, and L.T. Liu Tetrahedron Lett. 32 1991 3795 3798
34. A. Bernardi, S. Cardani, O. Carugo, L. Colombo, C. Scolastico, and R. Villa Tetrahedron Lett. 31 1990 2779 2782
35. S.F. Martin, and J.W. Corbett Synthesis 1992 55 56
36. Y. Morimoto, K. Nishida, Y. Hayashi, and H. Shirahama Tetrahedron Lett. 34 1993 5773 5776
37. S. Hanessian, and S. Raghavan Bioorg. Med. Chem. Lett. 4 1994 1697 1702
38. G. Casiraghi, P. Soro, G. Rassu, P. Spanu, L. Pinna, and F. Zanardi J. Org. Chem. 61 1996 5172 5174
39. G. Casiraghi, F. Zanardi, L. Battistini, M. Nespi, G. Rassu, P. Spanu, and M. Cornia Tetrahedron: Asymmetry 7 1996 1167 1180
40. G. Casiraghi, F. Zanardi, G. Rassu, and P. Spanu Chem. Rev. 95 1995 1677 1716
41. G. Casiraghi, F. Zanardi, G. Rassu, P. Spanu, and L. Pinna Tetrahedron Lett. 36 1995 1941 1944
42. G. Casiraghi, and G. Rassu Synthesis 1994 607 626
43. G. Casiraghi, G. Rassu, P. Spanu, and L. Pinna Tetrahedron Lett. 35 1994 2423 2426
44. G. Casiraghi, G. Rassu, P. Spanu, L. Pinna, and F. Ulgheri Tetrahedron Lett. 35 1994 4019 4022
45. G. Casiraghi, G. Rassu, P. Spanu, L. Pinna, and F. Ulgheri J. Org. Chem. 58 1993 3397 3400
46. G. Casiraghi, G. Rassu, P. Spanu, and L. Pinna J. Org. Chem. 57 1992 3760 3763
47. G. Casiraghi, L. Colombo, G. Rassu, and P. Spanu J. Org. Chem. 56 1991 6523 6527
48. G. Casiraghi, L. Colombo, G. Rassu, and P. Spanu J. Org. Chem. 56 1991 2135 2139
49. G. Casiraghi, L. Colombo, G. Rassu, and P. Spanu J. Org. Chem. 55 1990 2565 2567
50. G. Casiraghi, G. Rassu, L. Pinna, P. Spanu, N. Culeddu, G.G. Fava, M.B. Ferrari, and G. Pelosi Tetrahedron 48 1992 727 742
51. G. Casiraghi, L. Colombo, G. Rassu, P. Spanu, G.G. Fava, and M.F. Belicchi Tetrahedron 46 1990 5807 5824
52. G. Rassu, P. Spanu, G. Casiraghi, and L. Pinna Tetrahedron 47 1991 8025 8030
53. G. Rassu, G. Casiraghi, P. Spanu, and L. Pinna Tetrahedron: Asymmetry 3 1992 1035 1048
54. G. Casiraghi, L. Colombo, G. Rassu, and P. Spanu Tetrahedron Lett. 30 1989 5325 5328
55. G. Casiraghi, L. Colombo, G. Rassu, and P. Spanu J. Chem. Soc., Chem. Commun. 1991 603 604
56. H.B. Burgi, J.D. Dunitz, J.M. Lehn, and G. Wipff Tetrahedron 30 1974 1563
57. C.H. Heathcock, and L.A. Flippin J. Am. Chem. Soc. 105 1983 1667
58. R.W. Kierstead, A. Faraone, F. Mennona, J. Mullin, R.W. Guthrie, H. Crowley, B. Simlo, and L.C. Blaber J. Med. Chem. 26 1983 1561 1569
59. V. Jäger, and B. Häfele Liebigs Ann. Chem. 1987 85 87
60. R. Dumont, and H. Phander Helv. Chim. Acta 66 1983 814 823
61. D.Y. Jackson Synth. Commun. 18 1988 337 341
62. E.J. Corey, and A.J. Veukatesawarlu J. Am. Chem. Soc. 94 1972 6190
63. T. Mukaiyama, F. Tabusa, and K. Suzuki Chem. Lett. 1983 173 174
64. D.R. Williams, F.D. Klinger, E.E. Allen, and F.W. Lichtenthaler Tetrahedron Lett. 40 1988 5087 5090
65. D.L. Boger, J. Zhou, R.M. Borzirelli, S. Nukui, and S.L. Castle J. Org. Chem. 62 1997 2054 2069
66. 3)
67. Southard, J. M. Ph.D. Dissertation, Texas A&M University, 1997
68. B. Ernst, and C. Lehman Modern Synthetic Methods 1995 VCH New York pp 286-289
69. After the development of the procedure for the deprotection and free-basing of the independent α-anomer 20α, and the β-anomer 20β to produce 21α and 21β, a 193 mg (0.37 mmol) mixture (54:46 α/β) was subject to the same tandem of reactions affording 100 mg (64.1%) of 21α/21β as a mixture. Separation of these diastereomers using FLC proved difficult
70. 2.2 M HCl-EtOAc (concentrated) was prepared by bubbling gaseous HCl (lecture bottle) into anhydrous EtOAc for an extended period (about 3 min for 25 mL)
71. After the procedure for the preparation of carbamates 22α and 22β had been developed, an approximate 50/50 mixture of deprotected (i.e., Boc group removed) 21α/21β were subject to the same sequence of transformations (i.e., debenzylation, and Cbz-protection). A 91 mg (0.21 mmol) sample of 21 gave 62 mg (86.6%) of the 1° amine; the entire quantity of the 1° amine was protected as carbamate 22 as an inseparable mixture of C1 anomers (69.2 mg, 79.6%)