A flexible approach to methyl (5S)-5-alkyltetramate derivatives

Synlett

Volumn , Issue 2, 2009, Pages 297-301

  Jiang, Li Jiao ^a   Lan, Hong Qiao ^a   Zheng, Jian Feng ^a   Ye, Jian Liang ^a   Huang, Pei Qiang ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

Alkylation; Asymmetric synthesis; Grignard reagents; Reduction; Tetramates

Indexed keywords

EID: 62349111665     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1087672     Document Type: Article

References (95)

1. For reviews on tetramic acids, see: (a) Royles, B. J. L. Chem. Rev. 1995, 95, 1981.
2. (b) Henning, H.-G.; Gelbin, A. Advances in Tetramic Acid Chemistry, in Advances in Heterocyclic Chemistry, Vol. 57; Katritzky, A. R., Ed.; Academic Press: San Diego, 1993, 139.
3. (c) Ghisalberti, E. L. Bioactive Tetramic Acid Metabolites, In Studies in Natural Products Chemistry, Vol. 28, Part 9; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 2003, 109.
4. (d) Schobert, R. Naturwissenschaften 2007, 94, 1.
5. (e) Schobert, R.; Schlenk, A. Bioorg. Med. Chem. Lett. 2008, 16, 4203.
6. Aoki, S.; Higuchi, K.; Ye, Y.; Satari, R.; Kobayashi, M. Tetrahedron 2000, 56, 1833.
7. Unson, M. D.; Rose, C. B.; Faulkner, D. J.; Brinen, L. S.; Steiner, J. R.; Clardy, J. J. Org. Chem. 1993, 58, 6336.
8. Palk, S.; Carmeli, S.; Cullingham, J.; Moore, R. E.; Patterson, G. M. L.; Tius, M. A. J. Am. Chem. Soc. 1994, 116, 8116.
9. Hofheinz, W.; Oberhansli, W. E. Helv. Chim. Acta. 1977, 60, 660.
10. Suntornchashwej, S.; Suwanborirux, K.; Koga, K.; Isobe, M. Chem. Asian J. 2007, 2, 114.
11. Pettit, G. R.; Camano, Y.; Dufresne, C.; Cerny, R. L.; Herald, C. L.; Schmidt, J. M. J. Org. Chem. 1989, 54, 6005.
12. (a) Mita, A. C.; Hammond, L. A.; Bonate, P. L.; Weiss, G.; McCreery, H.; Syed, S.; Garrison, M.; Chu, Q. S.; DeBono, J. S.; Jones, C. B.; Weitman, S.; Rowinsky, E. K. Clin. Cancer Res. 2006, 12, 5207.
13. (b) Butler, M. S. Nat. Prod. Rep. 2005, 22, 162.
14. (a) Markopolou, O.; Markopoulos, J.; Nicholls, D. J. Inorg. Biochem. 1990, 39, 307.
15. (b) Heaton, B. T.; Jacob, C.; Markopoulos, J.; Markopoulou, O.; Nähring, J.; Skylaris, C.-K.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1996, 1701.
16. Kuramochi, H.; Nagata, S.; Itaya, H.; Matsubara, Y.; Sunoki, T.; Uchiro, H.; Takao, K.-I.; Kobayashi, S. Tetrahedron 2003, 59, 9743.
17. Yendapally, R.; Hurdle, J. G.; Carson, E. I.; Lee, R. B.; Lee, R. E. J. Med. Chem. 2008, 51, 1487.
18. Larbig, G.; Schmidt, B. J. Comb. Chem. 2006, 8, 480.
19. (a) Fitch, D. M.; Evans, K. A.; Chai, D.; Duffy, K. J. Org. Lett. 2005, 7, 5521.
20. (b) Evans, K. A.; Chai, D. P.; Graybill, T. L.; Burton, G.; Sarisky, R. T.; Lin-Goerke, J.; Johnston, V. K.; Rivero, R. A. Bioorg. Med. Chem. Lett. 2006, 16, 2205.
21. Zhu, Y. Q.; Liu, P.; Si, X. K.; Zou, X. M.; Liu, B.; Song, H. B.; Yang, H. Z. J. Agric. Food Chem. 2006, 54, 7200.
22. Courcambeck, J.; Bihel, F.; Michelis, C.; Quelever, G.; Kraus, J. L. J. Chem. Soc., Perkin Trans. 1 2001, 1421.
23. (a) Galeotti, N.; Poncet, J.; Chiche, L.; Jouin, P. J. Org. Chem. 1993, 58, 5370.
24. (b) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. Synlett 1996, 612.
25. (c) Wood, J. L.; Petsch, D. T.; Stoltz, B. M.; Hawkins, E. M.; Elbaum, D.; Stover, D. R. Synthesis 1999, 1529.
26. (d) Andrews, M. D.; Brewster, A. G.; Moloney, M. G. J. Chem. Soc., Perkin Trans. 1 2002, 80.
27. (e) Brennan, C. J.; Pattenden, G.; Rescourio, G. Tetrahedron Lett. 2003, 44, 8757.
28. (f) Page, P. C. B.; Hamzah, A. S.; Leach, D. C.; Allin, S. M.; Andrews, D. M.; Rassias, G. A. Org. Lett. 2003, 5, 353.
29. (g) Yoon-Miller, S. J. P.; Opalka, S. M.; Pelkey, E. T. Tetrahedron Lett. 2007, 48, 827.
30. (h) Hosseini, M.; Grau, J. S.; Sorensen, K. K.; Sotofte, I.; Tanner, D.; Murray, A.; Tonder, J. E. Org. Biomol. Chem. 2007, 5, 2207.
31. (a) Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1976, 49, 3287.
32. (b) Jouin, P.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1987, 1177.
33. (c) Schmidt, U.; Riedl, B.; Haas, G.; Grieaser, H.; Vetter, A.; Weinbrenner, S. Synthesis 1993, 216.
34. (d) Ma, D.; Ma, J.; Ding, W.; Dai, L. X. Tetrahedron: Asymmetry 1996, 7, 2365.
35. (e) Farran, D.; Youpet, L.; Martinez, J.; Dewynter, G. Org. Lett. 2007, 9, 4833.
36. For the synthesis of optically active tetramic acids and tetramates, see: (a) Klutchko, S.; O'Brien, P.; Hodges, J. C. Synth. Commun. 1989, 19, 2573.
37. (b) Jones, R. C. F.; Tankard, M. J. Chem. Soc., Perkin Trans. 1 1991, 240.
38. (c) Ley, S. V.; Smith, S. C.; Woodward, P. R. Tetrahedron 1992, 48, 1145.
39. (d) Fehrentz, J.-A.; Bourdel, E.; Califano, J.-C.; Chaloin, O.; Devin, C.; Garrouste, P.; Lima-Leite, A.-C.; Llinares, M.; Rieunier, F.; Vizavonna, J.; Winternitz, F.; Loffet, A.; Martinez, J. Tetrahedron Lett. 1994, 35, 1557.
40. (e) Leban, J. J.; Colson, K. L. J. Org. Chem. 1996, 61, 228.
41. (f) Detsi, A.; Markipoulos, J.; Igglessi-Markopoulou, O. Chem. Commun. 1996, 1323.
42. (g) Mattews, J.; Rivero, R. A. J. Org. Chem. 1998, 63, 4808.
43. (h) Kulkarni, B. A.; Ganesan, A. Tetrahedron Lett. 1998, 39, 4369.
44. (i) Andrews, M. D.; Brewster, A. G.; Crapnell, K. M.; Ibbett, A. J.; Jones, T.; Moloney, M. G.; Prout, K.; Watkin, D. J. Chem. Soc., Perkin Trans. 1 1998, 223.
45. (j) Detsi, A.; Micha-Screttas, M.; Igglessi-Markopoulou, O. J. Chem. Soc., Perkin Trans. 1 1998, 2443.
46. (k) Toyooka, N.; Nishio, M.; Shinoda, H.; Momose, T. Heterocycles 1999, 51, 1427.
47. (l) Detsi, A.; Afantitis, A.; Athanasellis, G.; Markopoulos, J.; Igglessi-Markopoulou, O.; Skylaris, C.-K. Eur. J. Org. Chem. 2003, 4593.
48. (m) Jones, R. C. F.; Pillainayagam, T. A. Synlett 2004, 2815.
49. (n) Schobert, R.; Dietrich, M.; Mullen, G.; Urbina-Gonzalez, J.-M. Synthesis 2006, 3902.
50. (o) Farran, D.; Parrot, I.; Martinez, J.; Dewynter, G. Angew. Chem. Int. Ed. 2007, 46, 7488; and references cited therein.
51. For the synthesis of optically active tetramic acid and tetramate natural products, see: (a) Ley, S. V.; Smith, S. C.; Woodward, P. R. Tetrahedron Lett. 1988, 29, 5829.
52. (b) Boeckman Jr, R. K.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036.
53. (c) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037.
54. (d) Pettit, G. R.; Thornton, T. J.; Mullaney, J. T.; Boyd, M. R.; Herald, D. L.; Singh, S.-B.; Flahive, E. J. Tetrahedron 1994, 50, 12097.
55. (e) Akaji, K.; Hayashi, Y.; Kiso, Y.; Kuriyama, N. J. Org. Chem. 1999, 64, 405.
56. (f) Longbottom, D. A.; Morrison, A. J.; Dixon, D. J.; Ley, S. V. Tetrahedron 2003, 59, 6955.
57. (g) Schobert, R.; Jagusch, C. Tetrahedron 2005, 61, 2301.
58. (h) Böhme, R.; Jung, G.; Breitmaier, E. Helv. Chim. Acta 2005, 88, 2837.
59. For non-amino acid based methods, see: (a) Banziger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010.
60. (b) Fustero, S.; Torre, M. G.; Danz-Cervera, J. F.; Arellano, C. R.; Piera, J.; Simon, A. Org. Lett. 2002, 4, 3651.
61. (a) Poncet, J.; Jouin, P.; Castro, B. J. Chem. Soc., Perkin Trans. 1 1990, 611.
62. (b) Petroliagi, M.; Igglessi-Markopoulou, O. Tetrahedron: Asymmetry 1999, 10, 1873.
63. (a) Hosseini, M.; Kringelum, H.; Murray, A.; Tonder, J. E. Org. Lett. 2006, 8, 2103.
64. (b) Suntornchashwej, S.; Suwanborirux, K.; Isobe, M. Tetrahedron 2007, 63, 3217.
65. For achiral and racemic examples, see: (a) Jones, R. C. F.; Bates, A. D. Tetrahedron Lett. 1986, 27, 5285.
66. (b) Jones, R. C. F.; Patience, J. M. J. Chem. Soc., Perkin Trans. 1 1990, 2350.
67. (c) Paintner, F. F.; Metz, M.; Baoschke, G. Synthesis 2003, 869.
68. (d) Hunter, R.; Richards, P. Synlett 2003, 271.
69. (e) Paintner, F. F.; Metz, M.; Bauschke, G. Synlett 2003, 627.
70. (f) Page, P. C. B.; Leach, D. C.; Hayman, C. M.; Hamzah, A. S.; Allin, S. M.; Mckee, V. Synlett 2003, 1025.
71. (a) Huang, P.-Q.; Wu, T.-J.; Ruan, Y.-P. Org. Lett. 2003, 5, 4341.
72. (b) Huang, P.-Q.; Deng, J. Synlett 2004, 247.
73. For racemic examples, see: (a) James, G. D.; Mills, S. D.; Pattenden, G. J. Chem. Soc., Perkin Trans. 1 1993, 2567.
74. (b) Issa, F.; Fischer, J.; Turner, P.; Coster, M. J. J. Org. Chem. 2006, 71, 4703.
75. For reviews on the use of (R)-phenylglycinol and other β-amino alcohols as chiral auxiliaries, see: (a) Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383.
76. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
77. (c) Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825.
78. For reviews, see: (a) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843.
79. (b) For selective examples, see: Escolano, C.; Amat, M.; Bosch, J. Chem. Eur. J. 2006, 8199.
80. (c) Burgess, L. E.; Meyers, A. I. J. Am. Chem. Soc. 1991, 113, 9858.
81. (d) Burgess, L. E.; Meyers, A. I. J. Org. Chem. 1992, 57, 1656.
82. (a) Chen, M.-D.; Zhou, X.; He, M.-Z.; Ruan, Y.-P.; Huang, P.-Q. Tetrahedron 2004, 60, 1651.
83. (b) Chen, M.-D.; He, M.-Z.; Zhou, X.; Huang, L.-Q.; Ruan, Y.-P.; Huang, P.-Q. Tetrahedron 2005, 60, 1335.
84. Reddy, P. Y.; Kondo, S.; Toru, T.; Ueno, Y. J. Org. Chem. 1997, 62, 2652.
85. Sahoo, M. K.; Mhaske, S. B.; Argade, N. P. Synthesis 2003, 346.
86. (a) Kursanov, D. N.; Parnes, Z. N.; Loim, N. M. Synthesis 1974, 633.
87. (b) Nagai, Y. Org. Prep. Proced. Int. 1980, 12, 13.
88. Ye, J.-L.; Huang, P.-Q.; Lü, X. J. Org. Chem. 2007, 72, 35.
89. For recent reviews on the N-acyliminium chemistry, see: (a) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
90. (b) Maryanoff, B. E.; Zhang, H. C.; Cohen, J. H.; Turchi, I. J.; Maryanoff, C. A. Chem. Rev. 2004, 104, 1431.
91. (c) Royer, J.; Bonin, M.; Micouin, L. Chem. Rev. 2004, 104, 2311.
92. Crystallographic data for 29h (CCDC 697420) and 26a (CCDC 697419) are available on request from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033, deposit@ccdc.cam.ac.uk].
93. 13C NMR spectral of new compounds are included in the supporting information.
94. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841; and references cited therein.
95. Ahn, N. T. Top. Curr. Chem. 1980, 88, 145.