Influence of steric parameters on the synthesis of tetramates from α-amino-β-alkoxy-esters and Ph3PCCO

Tetrahedron

Volumn 68, Issue 2, 2012, Pages 697-704

  Loke, Inga ^a   Park, Natja ^a   Kempf, Karl ^b   Jagusch, Carsten ^b   Schobert, Rainer ^b   Laschat, Sabine ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF BAYREUTH   (Germany)

Author keywords

Amino acids; Phosphorus ylides; Tetramic acids; Wittig olefination

Indexed keywords

4 (BENZYLOXY) 1 METHYL 5 [1 [(TRIISOPROPYLSILYL)OXY]ETHYL] 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 [(TERT BUTOXY)METHYL] 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 [(TRIETHYLSILYLOXY)METHYL] 1H PYRROL-2(5H) ONE; 4 (BENZYLOXY) 5 [(TRIISOPROPYLSILYLOXY)METHYL) 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 [1 (BENZYLOXY)ETHYL] 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 [1 (METHOXY)ETHYL] 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 [1 (TERT BUTYLOXY)ETHYL] 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 [1 [(TRIETHYLSILYL)OXY]ETHYL] 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 [1 [(TRIISOPROPYLSILYL)OXY]ETHYL] 1H 2(5H) ONE; 4 (BENZYLOXY) 5 [1 [(TRIISOPROPYLSILYL)OXY]ETHYL] 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 [[(TERT BUTYLDIMETHYLSILYL)OXY]METHYL] 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 ETHYLIDENE 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 ISOPROPYL 1H PYRROL 2(5H) ONE; 4 (BENZYLOXY) 5 METHYLENE 1H PYRROL 2(5H) ONE; 5 [1 (BENZYLOXY)ETHYL] 4 METHOXY 1 METHYL 1H PYRROL 2(5H) ONE; 5 S BUTYL 4 METHOXY 1 METHYL 1H PYRROL 2(5H) ONE; BENZOIC ACID; BENZYL 2 ACETAMIDO 3 (BENZYLOXY) 5 [(TERT BUTOXYCARBONYL)AMINO]PENTANOATE; BENZYL 2 ACETAMIDO 5 (TERT BUTOXYCARBONYLAMINO) 3 (TRIETHYLSILYLOXY)PENTANOATE; BENZYL 2 ACETAMIDO 5 (TERT BUTOXYCARBONYLAMINO) 3 (TRIISOPROPYLSILYLOXY)PENTANOATE; BENZYL 2 ACETAMIDO 5 (TERT BUTOXYCARBONYLAMINO) 3 [TERT BUTYL(DIMETHYL)SILYLOXY]PENTANOATE; CARBON; ESTER DERIVATIVE; N HYDROXYSUCCINIMIDE; TERT BUTYL [3 (BENZYLOXY) 3 [3 (BENZYLOXY) 5 OXO 2,5 DIHYDRO 1H PYRROL 2 YL]PROPYL]CARBAMATE; TERT BUTYL [3 [3 (BENZYLOXY) 5 OXO 2,5 DIHYDRO 1H PYRROL 2 YL]PROPYL]CARBAMATE; TETRAMIC ACID DERIVATIVE; THREONINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; ISOMERISM; PRIORITY JOURNAL;

EID: 82955249243     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.099     Document Type: Article

References (65)

1. O.I.-M.G. Athanasellis, and J. Markopoulos Bioinorg. Chem. Appl. 2010 1 11
2. R. Schobert, and A. Schlenk Bioorg. Med. Chem. 16 2008 4203 4221
3. P. Edwards Drug Discovery Today 12 2007 345 346
4. B.J.L. Royles Chem. Rev. 95 1995 1981 2001
5. H.-G. Henning, and A. Gelbin Adv. Heterocycl. Chem. 57 1993 139 185
6. B. Biersack, R. Diestel, C. Jagusch, F. Sasse, and R. Schobert J. Inorg. Biochem. 103 2009 72 76
7. T. Knoth, K. Warburg, C. Katzka, A. Rai, A. Wolf, A. Brockmeyer, O. Janning, T.F. Reubold, S. Eschenburg, D.J. Manstein, K. Hübel, M. Kaiser, and H. Waldmann Angew. Chem. 121 2009 7376 7381
8. Angew. Chem. Int. Ed. 48 2009 7240 7245
9. B. Biersack, R. Diestel, C. Jagusch, G. Rapp, G. Sasse, and R. Schobert Chem. Biodiv. 5 2008 2423 2430
10. R. Schobert, and C. Jagusch Tetrahedron 61 2005 2301 2307
11. S. Aoki, K. Higuchi, Y. Ye, R. Satari, and M. Kobayashi Tetrahedron 56 2000 1833 1836
12. R. Boehme, G. Jung, and E. Bretmaier Helv. Chim. Acta 88 2005 2837 2841
13. U. Marquardt, D. Schmid, and G. Jung Synlett 2000 1131 1132
14. A. Holtzel, M.G. Gänzle, G.J. Nicholson, W.P. Hamer, and G. Jung Angew. Chem. 39 2000 2766 2768
15. Angew. Chem. Int. Ed. 39 2000 2766 2768
16. M.G. Gänzle, A. Höltzel, J. Walter, G. Jung, and W.P. Hammer Appl. Environ. Microbiol. 66 2000 4325 4333
17. R. Schobert, M. Dietrich, G. Mullen, and J.-M. Urbina-Gonzalez Synthesis 22 2006 3902 3914
18. T. Yoshinari, K. Ohmori, M.G. Schrenz, A. Pfaltz, and K. Suzuki Angew. Chem. 122 2010 893 897
19. Angew. Chem., Int. Ed. 49 2010 881 885
20. B. Barnickel, and R. Schobert J. Org. Chem. 75 2010 6716 6719
21. C.V. Ramane, M.A. Mondal, V.G. Puranik, and M.K. Gurjar Tetrahedron Lett. 47 2006 4061 4064
22. P.R. Graupner, A. Carr, E. Clancy, J. Gilbert, K.L. Bailey, J.A. Derby, and B.C. Gerwick J. Nat. Prod. 66 2003 1558 1561
23. N. Cramer, S. Helbig, A. Baro, S. Laschat, R. Diestel, F. Sasse, D. Mathieu, C. Richter, G. Kummerlöwe, B. Luy, and H. Schwalbe ChemBioChem 9 2008 2474 2486
24. N. Cramer, M. Buchweiz, S. Laschat, W. Frey, A. Baro, D. Mathieu, C. Richter, and H. Schwalbe Chem. - Eur. J. 12 2006 2488 2503
25. A.C. Hart, and A.J. Philipps J. Am. Chem. Soc. 128 2006 1094 1095
26. N. Cramer, S. Laschat, A. Baro, H. Schwalbe, and C. Richter Angew. Chem. 117 2005 831 833
27. Angew. Chem., Int. Ed. 44 2005 820 822
28. S. Kanazawa, N. Fusetani, and S. Matsunaga Tetrahedron Lett. 34 1993 1065 1068
29. P.B. Kaparis, E. Hall, M. Ramstedt, W.R.J.D. Galloway, M. Welch, and D.R. Spring Chem. Commun. 2009 538 540
30. C.A. Lowery, J. Park, C. Gloeckner, M.M. Meijler, R.S. Mueller, H.I. Boskoff, R.L. Ulrich, C.E. Barry, D.E. Bartlett, V.V. Kravchenko, G.F. Kaufmann, and K.D. Janda J. Am. Chem. Soc. 131 2009 14473 14479
31. G.D. Gerke, J.C. O'Neill, D.M. Miller, R.J. Wezeman, M.E. Mattmann, Q. Lin, and H.E. Blackwell ChemBioChem 9 2008 389 400
32. J.T. Hodgkinson, M. Welch, and D.R. Spring ACS Chem. Biol. 2 2007 715 717
33. G.F. Kaufmann, R. Sartorio, S.-H. Lee, C.J. Rogers, M.M. Meijler, J.A. Moss, B. Clapham, A.P. Brogan, T.J. Dickerson, and K.D. Janda Proc. Natl. Acad. Sci. U.S.A. 102 2005 309 314
34. R.N. Lacey J. Chem. Soc. 1954 850 854
35. P. Jouin, B. Castro, and D. Nisato J. Chem. Soc., Perkin Trans. 1 1987 1177 1182
36. J.H. Spatz, S.J. Welsch, D.-E. Duhaut, N. Jäger, T. Bournier, M. Fredrick, L. Allmendinger, G. Ross, J. Kolb, C. Burdack, and M. Umkehrer Tetrahedron Lett. 50 2009 1705 1707
37. M. Anwar, and M.G. Maloney Tetrahedron Lett. 48 2007 7259 7262
38. A. Mallinger, B. Nadal, N. Chopin, and T. LeGall Eur. J. Org. Chem. 2010 1142 1148
39. M. Storgaard, F. Zaragoza Dörwald, B. Peschke, and D. Tanner J. Org. Chem. 74 2009 5032 5040
40. D. Farran, I. Parrot, J. Martinez, and G. Dewynter Angew. Chem. 119 2007 7632 7634
41. Angew. Chem., Int. Ed. 46 2007 7488 7489
42. D. Matiadis, and O. Igglesi-Markopoulou Eur. J. Org. Chem. 2010 5989 5995
43. K.C. Prousis, J. Markopoulos, V. McKee, and O. Igglessi-Markopoulou Tetrahedron 66 2010 3944 3950
44. N. Riache, C. Bailly, A. Deville, L. Dubost, and B. Nay Eur. J. Org. Chem. 2010 5402 5408
45. B. Alcaide, P. Almendros, A. Luna, and M.R. Torres Adv. Synth. Catal. 352 2010 621 626
46. W. Hofheinz, and W.E. Oberhänsli Helv. Chim. Acta 60 1977 660 669
47. P.G. Williard, and S.E. De Laszlo J. Org. Chem. 49 1984 3489 3493
48. H. Köhler, and H. Gerlach Helv. Chim. Acta 67 1984 1783 1792
49. R.C.F. Jones, and A.D. Bates Tetrahedron Lett. 27 1986 5285 5288
50. R. Hunter, S.C.M. Rees-Jones, and H. Su Tetrahedron Lett. 48 2007 2819 2822
51. M.D. Clift, and R.J. Thomson J. Am. Chem. Soc. 131 2009 14579 14583
52. T. Sengoku, J. Wierzejska, M. Takahashi, and H. Yoda Synlett 2010 2944 2946
53. H.J. Bestmann, and W. Kellermann Synthesis 1994 1257 1261
54. H.J. Bestmann, M. Schmidt, and R. Schobert Synthesis 1988 49 53
55. H.J. Bestmann, and R. Schobert Angew. Chem. 97 1985 783 784
56. Angew. Chem., Int. Ed. Engl. 24 1985 791 792
57. H.J. Bestmann, and D. Sandmeier Angew. Chem. 87 1975 630
58. Angew. Chem. Int. Ed. Engl. 14 1975 634
59. R. Schobert, and C. Jagusch Tetrahedron 61 2005 2301 2307
60. R. Schobert, C. Jagusch, C. Melanophy, and G. Mullen Org. Biomol. Chem. 2 2004 3524 3529
61. B. Barnickel, F. Bayliffe, R. Diestel, K. Kempf, S. Laschat, S. Pachali, F. Sasse, A. Schlenk, and R. Schobert Chem. Biodiv. 7 2010 2830 2845
62. J. Henderson, and A. Phillips Angew. Chem. 120 2008 8627 8629
63. Angew. Chem., Int. Ed. 47 2008 8499 8501
64. M.A. Bae, K. Yamada, Y. Ijuin, T. Tsuji, K. Yazawa, Y. Tomono, and D. Uemura Heterocycl. Commun. 2 1996 315 318
65. E. Vedejs, and C.F. Marth J. Am. Chem. Soc. 110 1988 3948 3958