Synthesis of a regular 24-membered cyclodepsipeptide by direct amide cyclization

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 64, Issue 6, 2009, Pages 689-698

  Köttgen, Peter ^a   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Aminoisobutyric acid; Azirine oxazolone method; Crystal structure; Cyclodepsipeptides; Direct amide cyclization

Indexed keywords

AMIDES; AMINO ACIDS; CHLORINE COMPOUNDS; CRYSTAL STRUCTURE;

ALPHA-AMINO ACIDS; ALTERNATING SEQUENCES; AMINOISOBUTYRIC ACID; AZIRINE/OXAZOLONE METHOD; CYCLIC DEPSIPEPTIDES; CYCLODEPSIPEPTIDES; LINEAR PRECURSORS; MACROLACTONIZATION;

CYCLIZATION;

EID: 67749130969     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2009-0615     Document Type: Article

References (98)

1. a) H. Vervoort, W. Fenical, R. de Epifanio, J. Org. Chem. 2000, 65, 782-792;
2. b) N. Sitachitta, R. T. Williamson, W. H. Gerwick, J. Nat. Prod. 2000, 63, 197-200;
3. c) F.D. Horgan, D.B. de los Santos, G. Goetz, B. Sakamoto, Y. Kan, H. Nagai, P. J. Scheuer, J. Nat. Prod. 2000, 63, 152-154;
4. d) K. Fujii, K. Sivinen, E. Naganawa, K. Harada, Tetrahedron 2000, 56, 725-733;
5. e) A.K. Gosh, A. Bischoff, Org. Lett. 2000, 2, 1573-1575;
6. f) H. Luesch, R. Pangilinan, W.Y. Yoshida, R. E. Moore, V. J. Paul, J. Nat. Prod. 2001, 64, 304-307;
7. g) F. Sarabia, S. Chammaa, F. J. Lopez-Herrera, Tetrahedron Lett. 2002, 43, 2961-2965;
8. h) J. Hong, L. Zhang, Frontiers of Biotechnology & Pharmaceuticals 2002, 3, 193-199;
9. i) H. Luesch, P. G. Williams, W.Y. Yoshida, R. E. Moore, V. J. Paul, J. Nat. Prod. 2002, 65, 996-1000;
10. k) Y. J. Feng, J.W. Blunt, A. L. J. Cole, J. F. Cannon, W. T. Robinson, M.H.G. Munro, J. Org. Chem. 2003, 68, 2002-2005;
11. l) G. Bringmann, G. Lang, S. Steffens, K. Schaumann, J. Nat. Prod. 2004, 67, 311-315;
12. m) C.-H. Chen, G. Lang, M. Mitova, A.C. Murphy, A. L. J. Cole, L.B. Din, J.W. Blunt, M.H.G. Munro, J. Org. Chem. 2006, 71, 7947-7951.
13. a) H. Huang, Z. She, Y. Liu, L. L. P. Vrijmoed, W. Lin, J. Nat. Prod. 2007, 70, 1696-1699;
14. b) C. M. Boot, T. Amagata, K. Tenney, J. E. Compton, H. Pietraszkiewicz, F. A. Valerrote, P. Crews, Tetrahedron 2007, 63, 9903-9914;
15. c) S. P. Gunasekera, R. Ritson-Williams, V. J. Paul, J. Nat. Prod. 2008, 71, 2060-2063;
16. d) K. Taori, V. J. Paul, H. Luesch, J. Nat. Prod. 2008, 71, 1625-1629;
17. e) Z. Yu, G. Lang, I. Kajahn, R. Schmaljohann, J. F. Imhoff, J. Nat. Prod. 2008, 71, 1052-1054;
18. f) D. Dwivedi, R. Jansen, G. Molinari, M. Nimtz, B. N. Johri, V. Wray, J. Nat. Prod. 2008, 71, 637-641;
19. g) K. Taori, V. J. Paul, H. Luesch, J. Am. Chem. Soc. 2008, 130, 1806-1807.
20. a) K. Brockmann, G. Schmidt-Kastner, Chem. Ber. 1955, 88, 57-61;
21. b) M. M. Shemyakin, N.A. Aldanova, R. I. Vinogradova, V.Y. Feigina, Tetrahedron Lett. 1963, 28, 1921-1925;
22. c) B.C. Pressman, E. J. Harris, W. S. Jagger, J.N. Johnson, Procl. Nat. Acad. Sci. U.S.A. 1967, 58, 1949-1956.
23. a) Y.A. Ovchinnikov, V. T. Ivanov, A.V. Evstratov, I. I. Mikhaleva, V. F. Bystrov, S.L. Portnova, T. A. Balashova, E.N. Meshcheryakova, V. M. Tul'chinskii, Int. J. Pept. Protein Res. 1974, 6, 465-498;
24. b) P. Jeschke, W. Etzel, A. Harder, M. Schindler, A. Gohrt, U. Pleiss, H. Kleinkauf, R. Zocher, G. Thielking, W. Gau, G. Bonse, Bioorg. Chem. 1999, 207-214;
25. c) S. Firáková, B. Proksa, M. Sturdikova, Pharmazie 2007, 62, 563-568;
26. d) M. Jestoi, Crit. Rev. Food Sci. Nutr. 2008, 48, 21-49.
27. B.C. Pressman, Ann. Rev. Biochem. 1976, 45, 501-530.
28. a) M. Krause, A. Lindemann, M. Glinski, T. Hornbogen, G. Bonse, P. Jeschke, G. Thielking, W. Gau, R. Zocher, J. Antibiot. 2001, 54, 797-804;
29. b) A. Logrieco, A. Rizzo, R. Ferracane, A. Ritieni, Appl. Environ. Microbiol. 2002, 82-85;
30. c) Y. Lin, J. Wang, X. Wu, S. Zhou, L. L. P. Vrijmoed, E.B.G. Jones, Austral. J. Chem. 2002, 55, 225-227;
31. d) C. Nilanonta, M. Isaka, R. Chanphen, N. Thong-orn, M. Tanticharoen, Y. Thebtaranonth, Tetrahedron 2003, 59, 1015-1020;
32. e) P. Vongvilai, M. Isaka, P. Kittakoop, P. Srikitikulchai, P. Kongsaeree, S. Prabpai, Y. Thebtaramonth, Helv. Chim. Acta 2004, 87, 2066-2073;
33. f) A. Pohanka, K. Capieau, A. Broberg, J. Stenlid, E. Stenström, L. Kenne, J. Nat. Prod. 2004, 67, 851-857;
34. g) K. Hiraga, S. Yamamoto, H. Fukuda, N. Hamanaka, K. Oda, Biochem. Biophys. Res. Commun. 2005, 328, 1119-1125;
35. h) L. Ivanova, E. Skjerve, G. S. Eriksen, S. Uhlig, Toxicon 2006, 47, 868-857;
36. i) S.C. Feifel, T. Schmiederer, T. Hornbogen, H. Berg, R.D. Süssmuth, R. Zocher, Chem-Bio Chem 2007, 8, 1767-1770;
37. k) H.-H. Song, H.-S. Lee, J.-H. Jeong, H.-S. Park, C. Lee, Int. J. Food. Microbiol. 2008, 122, 296-301;
38. l) J. Müller, S. C. Feifel, T. Schmiederer, R. Zocher, R.D. Süssmuth, Chem-Bio Chem 2009, 10, 323-328.
39. a) A.M. Sefler, M.C. Kozlowski, T. Guo, P.A. Bartlett, J. Org. Chem. 1977, 62, 93-102;
40. b) Y. L. Dory, J. M. Mellor, J. F. McAleer, Tetrahedron Lett. 1996, 52, 1343-1360;
41. c) T. Imaeda, Y. Hamada, T. Shioiri, Tetrahedron Lett. 1994, 35, 591-594;
42. d) N. Bisek, S. Wetzel, H.-D. Arndt, H. Waldmann, Chem. Eur. J. 2008, 14, 8847-8860;
43. e) K. J. Hale, S. Manaviazar, L. Lazarides, J. George, M. A. Walters, J. Cai, V.M. Delisser, G.S. Bhatia, S.A. Peak, S.M. Dalbey, A. Lefranc, Y.-N. P. Chen, A.W. Wood, P. Crowe, P. Erwin, M. El-Tamani, Org. Lett. 2009, 11, 737-740.
44. a) S. Cerrini, E. Gavuzzo, G. Luisi, F. Pinnen, Int. J. Pept. Protein Res. 1993, 41, 282-290;
45. b) Y. Hirai, K. Yokota, T. Momose, Heterocycles 1994, 39, 603-612;
46. c) K.W. Li, J. Wu, W. Xing, J.A. Simpson, J. Am. Chem. Soc. 1996, 118, 7237-7238;
47. d) G. R. Pettit, S. Hu, J.C. Knight, J.-C. Chapuis, J. Nat. Prod. 2009, Doi: 10.1021/np800607x.
48. a) D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1984, 67, 526-533;
49. b) D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1987, 70, 329-338;
50. c) D. Obrecht, H. Heimgartner, Helv. Chim. Acta 1990, 73, 221-228.
51. J.M. Villagordo, H. Heimgartner, Helv. Chim. Acta 1997, 80, 748-766.
52. H. Heimgartner, F. S. Arnhold, S. Fritschi, K.N. Koch, A. Linden, J. E. F. Magirius, Lectures Heterocycl. Chem. 1999, 36, 1539-1547.
53. a) K.N. Koch, A. Linden, H. Heimgartner, Helv. Chim. Acta 2000, 83, 233-257;
54. b) K.N. Koch, H. Heimgartner, Helv. Chim. Acta 2000, 83, 1881-1900;
55. c) K.N. Koch, A. Linden, H. Heimgartner, Tetrahedron 2001, 57, 2311-2326;
56. d) K.N. Koch, G. Hopp, A. Linden, K. Moehle, H. Heimgartner, Helv. Chim. Acta 2001, 84, 502-512.
57. a) B. Iliev, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 3215-3234;
58. b) B. Iliev, A. Linden, R.W. Kunz, H. Heimgartner, Tetrahedron 2006, 62, 1079-1094.
59. J. E. F. Magirius, PhD Thesis, Universität Zürich, 1995.
60. P. Köttgen, A. Linden, H. Heimgartner, Helv. Chim. Acta 2006, 89, 731-746.
61. H. Heimgartner, Angew. Chem. 1991, 103, 271-297.
62. Angew. Chem., Int. Ed. Engl. 1991, 30, 238-264.
63. a) P. Wipf, H. Heimgartner, Helv. Chim. Acta 1990, 73, 13-24;
64. b) R. Luykx, C.B. Bucher, A. Linden, H. Heimgartner, Helv. Chim. Acta 1996, 79, 527-540;
65. c) R. T.N. Luykx, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 4093-4111;
66. d) N. Pradeille, H. Heimgartner, J. Pept. Sci. 2003, 9, 827-837;
67. e) N. Pradeille, O. Zerbe, K. Möhle, A. Linden, H. Heimgartner, Chem. Biodivers. 2005, 2, 1127-1152;
68. f) W. Altherr, A. Linden, H. Heimgartner, Chem. Biodivers. 2007, 4, 1144-1169.
69. a) J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1998, 54, 8721-8736;
70. b) J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1999, 55, 5359-5376;
71. c) J. Lehmann, A. Linden, H. Heimgartner, Helv. Chim. Acta 1999, 82, 888-908;
72. d) J. Lehmann, A. Linden, H. Heimgartner, Helv. Chim. Acta 1999, 82, 1899-1915;
73. e) A. Budzowski, A. Linden, H. Heimgartner, Helv. Chim. Acta 2008, 91, 1471-1488;
74. A. Bärtsch, B. Bischof, H. Heimgartner, Pol. J. Chem. 2009, 83, 195-206.
75. a) F. S. Arnhold, PhD Thesis, Universität Zürich, 1997;
76. b) T. Jeremic, A. Linden, H. Heimgartner, Helv. Chim. Acta 2004, 87, 3056-3079;
77. c) T. Jeremic, A. Linden, H. Heimgartner, Chem. Biodiv. 2004, 1, 1730-1761;
78. d) T. Jeremic, A. Linden, K. Moehle, H. Heimgartner, Tetrahedron 2005, 61, 1871-1883;
79. e) T. Jeremic, A. Linden, H. Heimgartner, J. Pept. Sci. 2008, 14, 1051-1061;
80. f) I. Dannecker-Dörig, A. Linden, H. Heimgartner, Collect. Czech. Chem. Commun. 2009, in press.
81. P. Eckenberg, U. Groth, T. Huhn, N. Richter, C. Schmeck, Tetrahedron 1993, 49, 1619-1624.
82. C.K. Johnson, ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, TN (USA) 1976.
83. J. Bernstein, R. E. Davis, L. Shimoni, N.-L. Chang, Angew. Chem. 1995, 107, 1689-1708;
84. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555-1573.
85. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1986, 69, 1153-1162.
86. K.C. Nicolaou, Tetrahedron 1977, 33, 683-710.
87. M. H. Chisholm, J. C. Gallucci, H. Yin, PNAS 2006, 103, 15315-15320.
88. V. Srirajan, A.R.A. S. Deshmukh, V.G. Puranik, B. M. Bhawal, Tetrahedron: Asymmetry 1996, 7, 2733-2738.
89. R. Hooft, COLLECT, Nonius Kappa CCD Software, Nonius BV, Delft (The Netherlands) 1999.
90. CCDC 725269 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre, via www.ccdc.cam.ac.uk/data request/cif.
91. HKL DENZO, SCALEPACK, Z. Otwinowski, W. Minor, in Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A (Eds.: C.W. Carter, Jr., R. M. Sweet), Academic Press, New York, 1997, pp. 307-326.
92. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, A Program for the Automatic Solution of Crystal Structures by Direct Methods; see: J. Appl. Crystallogr. 1994, 27, 435.
93. E. N. Maslen, A.G. Fox, M. A. O'Keefe, in International Tables for Crystallography, Vol. C (Ed.: A. J. C. Wilson), Kluwer Academic, Dordrecht, 1992; pp. 477-486; Table 6.1.1.1.
94. R. F. Stewart, E.R. Davidson, W.T. Simpson, J. Chem. Phys. 1965, 42, 3175-3187.
95. J.A. Ibers, W.C. Hamilton, Acta Crystallogr. 1964, 17, 781-782.
96. D. C. Creagh, W. J. McAuley, in International Tables for Crystallography, Vol. C (Ed.: A. J.C. Wilson), Kluwer Academic, Dordrecht, 1992; pp. 219-222; Table 4.2.6.8.
97. D. C. Creagh, J.H. Hubbell, in International Tables for Crystallography, Vol. C (Ed.: A. J.C. Wilson), Kluwer Academic, Dordrecht, 1992; pp. 200-206; Table 4.2.4.3.
98. G. M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Göttingen (Germany) 1997.