5-Aminooxazole as an internal traceless activator of C-terminal carboxylic acid: Rapid access to diversely functionalized cyclodepsipeptides

Chemistry - A European Journal

Volumn 12, Issue 4, 2006, Pages 1174-1184

  Bughin, Carine ^a   Zhao, Gang ^a   Bienaymé, Hugues ^b   Zhu, Jieping ^a  

^a CNRS   (France)

^b INSTITUT DE RECHERCHE PIERRE FABRE   (France)

Author keywords

Cyclization; Domino reactions; Macrocycles; Multicomponent reactions; Peptides

Indexed keywords

CHEMICAL ACTIVATION; KETONES; POLYPEPTIDES; SALTS; SULFUR; SYNTHESIS (CHEMICAL);

CYCLIZATION; DOMINO REACTIONS; MACROCYCLES; MULTICOMPONENT REACTIONS; PEPTIDES;

CARBOXYLIC ACIDS;

CARBOXYLIC ACID; DEPSIPEPTIDE; OXAZOLE DERIVATIVE; SPIRONOLACTONE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

CARBOXYLIC ACIDS; CYCLIZATION; DEPSIPEPTIDES; OXAZOLES; SPIRONOLACTONE; TRIFLUOROACETIC ACID;

EID: 31344466498     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500703     Document Type: Article

References (148)

1. a) F. Sarabia, S. Chammaa, A. S. Ruiz, L. M. Oritz, F. J. L. Herrera, Curr. Med. Chem. 2004, 11, 1309-1332;
2. b) C. E. Ballard, H. Yu, B. Wang, Curr. Med. Chem. 2002, 9, 471-498;
3. c) Y. Q. Tang, J. Yuan, G. Osapay, K. Osapay, D. Tran, C. J. Miller, A. J. Quellete, M. E. Selsted, Science 1999, 286, 498-502;
4. d) N. Fusetani, S. Matsunaga, Chem. Rev. 1993, 93, 1793-1806.
5. a) H. Kessler, Angew. Chem. 1982, 94, 509-520;
6. Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523;
7. b) C. Toniolo, Int. J. Peptide Protein Res. 1990, 35, 287-300.
8. a) D. P. Fairlie, G. Abbenante, D. R. March. Curr. Med. Chem. 1995, 2, 654-686;
9. b) L. A. Wessjohann, E. Ruijter, Top. Curr. Chem. 2005. 243, 137-184.
10. a) D. F. Verber, R. M. Freidinger, Trends Neurosci. 1985, 8, 392-396;
11. b) E. Milner-White, J. Trends Pharmacol. Sci. 1989, 10, 70-74;
12. c) J. S. Davies, J. Pept. Sci. 2003, 9, 471-501.
13. K. Burgess, Acc. Chem. Res. 2001, 34, 826-835.
14. a) J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243-2266;
15. b) F. Albericio, R. Chinchilla, D. J. Dodsworth, C. Najera, Org. Prep. Proc. Int. 2001, 33, 203-303.
16. For recent reviews, see a) P. Li, P. Roller, J. Xu, Curr. Org. Chem. 2002, 6, 411-440;
17. b) J. N. Lambert, J. P. Mitchell, K. D. Roberts, J. Chem. Soc. Perkin Trans. 1 2001, 471-484;
18. c) P. Wipf, Chem. Rev. 1995, 95, 2115-2134.
19. F. Cavelier-Frontin, G. Pèpe, J. Verducci, D. Siri, R. Jacquier, J. Am. Chem. Soc. 1992, 114, 8885-8890.
20. For recent solid-phase syntheses of cyclopeptides, see a) H. Mihara, S. Yamabe, T. Niidome, H. Aoyagi, H. Kumagai, Tetrahedron Lett. 1995, 36, 4837-4840;
21. b) A. F. Spatola, K. Darlak, P. Romanovskis, Tetrahedron Lett. 1996, 37, 591-594;
22. c) A. F. Spatola, Y. Crozet, D. DeWitt, M. Yanagisawa, J. Med. Chem. 1996, 39, 3842-3846;
23. d) K. Burgess, D. Lim, M. Bois-Choussy, J. Zhu, Tetrahedron Lett. 1997, 38, 3345-3348;
24. e) C. L. Lanter, J. W. Guiles, R. A. Rivero, Mol. Diversity 1999, 4, 149-153;
25. f) H. K. J. Jensen, J. Alsina, M. F. Songster, J. Vágner, F. Albericio, G. Barany, J. Am. Chem. Soc. 1998, 120, 5441-5442;
26. g) Y. Feng, M. Pattarawarapan, Z. Wang, K. Burgess, Org. Lett. 1999, 121-124;
27. h) G. Bourne, W. D. F. Meutermans, P. F. Alewood, R. McGeary, M. Scanlon, A. Watson, M. L. Smyth, J. Org. Chem. 1999, 64, 3095-3101;
28. i) A. J. Souers, A. A. Virgilio, Å. Rosenquist, W. Fenuik, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 1817-1825;
29. j) C. Hasakell-Luevano, Å. Rosenquist, A. J. Souers, K. C. Khong, J. A. Ellman, R. D. Cone, J. Med. Chem. 1999, 42, 4380-4387;
30. k) C. F. Bleczinski, C. Richert, Org. Lett. 2000, 2. 1697-1700;
31. l) S. Terracciano, I. Bruno, G. Bifulco, J. E. Copper, C. D. Smith, L. Gomez-Paloma, R. Riccio, J. Nat. Prod. 2004, 67, 1325-1331;
32. m) V. Wittmann, S. Secberger, Angew. Chem. 2004, 116, 918-921:
33. Angew. Chem. Int. Ed. 2004, 43, 900-909;
34. n) a combinatorial library of cyclopeptide produced by Ladybird Beetle: F. C. Schroeder, J. J. Farmer, S. R. Smedley, A. B. Attygalle, T. Eisner, J. Meinwald, J. Am. Chem. Soc. 2000, 122, 3628-3634.
35. a) B. E. Evans, K. E. Rittle, M. G. Bock, R. M. DiPardo, R. M. Frcidinger, W. L. Whitter, G. F. Lundell, D. F. Veber, P. S. Anderson, R. S. L. Chang, V. J. Lotti, D. J. Cerino, T. B. Chen, P. J. Kling, K. A. Kunkel, J. P. Springer, J. Hirshfield, J. Med. Chem. 1988, 31, 2235-2246;
36. b) D. A. Horton, G. T. Bourner, M. L. Smythe, Chem. Rev. 2003, 103, 893-930.
37. a) D. A. Horton, G. T. Bourner, M. L. Smythe, J. Comput.-Aided Mol. Design 2002, 16, 415-430.
38. Reviews: a) J. Zhu, Exp. Opin. On Therap. Patents 1999, 9, 1005-1019;
39. b) D. Kahne, C. Leimkuhler, W. Lu, C. T. Walsh, Chem. Rev. 2005, 105, 425-448.
40. New synthetic strategy: a) P. Botli, T. D. Pallin, J. P. Tam, J. Am. Chem. Soc. 1996, 118, 10018-10024;
41. b) L. Zhang, J. P. Tam, J. Am. Chem. Soc. 1997, 119, 2363-2370;
42. c) Y. Shao, W. Lu, S. B. H. Kent, Tetrahedron Lett. 1998, 39, 3911-3914;
43. d) J. A. Camarero, J. Pavel, T. W. Muir, Angew. Chem. 1998, 110, 361-364;
44. Angew. Chem. Int. Ed. Engl. 1998, 37, 347-349;
45. e) J. P. Tam, Y.-A. Lu, Q. Yu, J. Am. Chem. Soc. 1999, 121, 4316-4324;
46. f) J. P. Tam, Y.-A. Lu, J. L. Yang, K. W. Chiu, Proc. Nat. Acad. Sci. USA 1999, 96, 8913-8918;
47. g) L. Z. Yang, P. E. Dawson, J. Am. Chem. Soc. 2001, 123, 526-533;
48. h) W. D. F. Meutermans, S. W. Golding, G. T. Bourne, L. P. Miranda, M. J. Dooley, P. F. Alewood, M. L. Smythe, J. Am. Chem. Soc. 1999, 121, 9790-9796;
49. i) W. D. F. Meutermans, G. T. Bourne, S. W. Golding, D. A. Horton, M. R. Campitelli, D. Craik, M. Scanlon, M. L. Smythe, Org. Lett. 2003, 5, 2711-2714;
50. j) O. David, W. J. N. Meester, H. Bierâugel, H. E. Schoemaker, H. Hiemstra, J. H. van Maarseveen, Angew. Chem. 2003, 115, 4509-4375:
51. Angew. Chem. Int. Ed. Engl. 2003, 42, 4373-4375;
52. k) W. Kurosawa, H. Kobayashi, T. Kan, T. Fukuyama, Tetrahedron 2004, 60, 9615-9628.
53. Synthesis of macrocycles with an endo biaryl ether bond: a) Zhu, J. Synlett 1997, 133-144. Synthesis of macrocycles with an endo aryl-aryl bond;
54. b) A. C. Carbonnelle, J. Zhu, Org. Lett. 2000, 2, 3477-3480;
55. c) M. Bois-Choussy, P. Cristau, J. Zhu, Angew, Chem. 2003, 115, 4370-4373;
56. Angew. Chem. Int. Ed. 2003, 42, 4238-4241;
57. d) R. Lépine, J. Zhu, Org. Lett. 2005, 7, 2981-2984. Multicomponent synthesis of cyclophane;
58. e) P. Janvier, M. Bois-Choussy, H. Bienaymé, J. Zhu, Angew. Chem. 2003, 115, 835-838:
59. Angew. Chem. Int. Ed. 2003, 42, 811-814.
60. Generation of active β-acyl ketene by thermal cycloreversion of 2,2-dimethyl-1,3-dioxin-2-one followed by intramolecular trapping of the ketene by tethered alcohol leading to β-keto lactones under neutral conditions: a) R. K. Boeckman, Jr., J. R. Pruitt, J. Am. Chem. Soc. 1989, 111, 8286-8288;
61. b) C. Chen, E. K. Quinn, M. M. Olmstead, M. J. Kurth, J. Org. Chem. 1993, 58, 5011-5014;
62. c) B. M. Trost, J. L. Gunzner, J. Am. Chem. Soc. 2001, 123, 9449-9450.
63. a) X. Sun, P. Janvier, G. Zhao, H. Bienaymé, J. Zhu, Org. Lett. 2001. 3, 877-880;
64. b) P. Janvier, X. Sun, H. Bienaymé, J. Zhu, J. Am. Chem. Soc. 2002, 124, 2560-2567.
65. For recent reviews on multicomponent reactions, sec a) A. Dömling, Curr. Opin. Chem. Biol. 2002, 6, 306-314;
66. b) C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51-80;
67. c) R. V. A. Orru, M. De Greef, Synthesis 2003, 1471-1499;
68. d) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101-4111;
69. e) A. Jacobi von Wangelin, H. Neumann, D. Gördes, S. Klaus, D. Strübing, M. Beller, Chem. Eur. J. 2003, 9, 4286-4294;
70. f) M. Murakami, Angew. Chem. 2003, 115, 742-744;
71. Angew. Chem. Int. Ed. 2003, 42, 718-720;
72. g) J. Zhu, Eur. J. Org. Chem. 2003, 1133-1144;
73. h) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957-4980;
74. i) for a recent hook, see Multicomponent Reaction (Eds.: J. Zhu, H. Bienaymé), Wiley-VCH, Weinheim, 2005.
75. Preliminary result has been published as a communication: G. Zhao, X. Sun, H. Bienaymé, J. Zhu, J. Am. Chem. Soc. 2001, 123, 6700-6701.
76. a) D. Clern, J. P. Fleury, Bull. Soc. Chim. Fr. 1974, 211-217;
77. b) D. Clern, G. Kille, J. P. Fleury, Tetrahedron 1974, 30, 469-474.
78. a) B. H. Lipshutz, R. W. Hungate, K. E. McCarthy, Tetrahedron Lett. 1983, 24, 5155-5158;
79. b) B. H. Lipshutz, R. W. Hungate, K. E. Mc-Carthy, J. Am. Chem. Soc. 1983, 105, 7703-7713;
80. c) B. H. Lipshutz, B. E. Huff, K. E. McCarthy, T. A. Miller, S. M. J. Mukarram, T. J. Siahaan, W. D. Vaccaro, H. Webb, A. M. Falick, J. Am. Chem. Soc. 1990, 112, 7032-7041.
81. a) M. Joullié. D. J. Richard, Chem. Commun. 2004, 2011-2015;
82. b) T. Temal-Laïb, J. Chastanct, J. Zhu, J. Am. Chem. Soc. 2002, 124, 583-590;
83. c) P. Cristau, T. Temal-Laïb, M. Bois-Choussy, M. T. Martin, J. P. Vors, J. Zhu, Chem. Eur. J. 2005, 11, 2668-2679, and references therein.
84. For reviews on domino process, see a) P. A. Wender, B. L. Miller, Organic Synthesis: Theory and Applications 1993, 2, 27-66;
85. b) B. M. Trost, Angew. Chem. 1995, 107, 285-307;
86. Angew. Chem. Int. Ed. Engl. 1995, 34, 259-281;
87. c) L. F. Tietze, Chem. Rev. 1996, 96. 115-136;
88. d) A. Padwa, M. D. Weingarten, Chem. Rev. 1996, 96, 223-270;
89. e) S. E. Denmark, A. Thorarensen, Chem. Rev. 1996, 96, 137-165;
90. f) J. D. Winkler, Chem. Rev. 1996, 96, 167-176;
91. g) M.-H. Filippini, J. Rodriguez, Chem. Rev. 1999, 99, 27-76;
92. h) G. Poli, G. Giambastiani, A. Heumann, Tetrahedron 2000, 56, 5959-5989;
93. i) L. F. Tietze, F. Haunert in Stimulating Concepts in Chemistry (Eds.: M. Shibasaki, J. F. Stoddart, F. Vögtle), Wiley-VCH, Weinheim, 2000, pp. 39-64;
94. j) G. Zeni, R. C. Larock, Chem. Rev. 2004, 104, 2285-2310.
95. H. H. Wasserman, K. E. Mccarthy, K. S. Prowse, Chem. Rev. 1986, 86, 845-856.
96. For a review, see H. Heimgartner, F. S. Arnhold, S. P. Fritschi, K. N. Koch, J. E. F. Magirius, A. Linden, J. Heterocyclic Chem. 1999, 36, 1539-1547.
97. a) D. Obrecht, H. Heimgartner, Helv. Chim. Acta. 1984, 67, 526-533;
98. b) D. Obrecht, H. Heimgartner, Helv. Chim. Acta. 1987, 70, 329-339;
99. c) D. Obrecht, H. Heimgartner, Helv. Chim. Acta. 1990, 73, 221-228;
100. d) J. M. Villalgordo, H. Heimgartner, Helv. Chim. Acta. 1997, 80, 748-767;
101. e) K. N. Koch, A. Linden, H. Heimgartner, Helv. Chim. Acta. 2000, 83, 233-257, and references therein.
102. a) P. Michael, G. Pattenden, Angew. Chem. 1993, 105, 1-23;
103. Angew. Chem. Int. Ed. 1993, 32, 1-23;
104. b) M. Garson, Chem. Rev. 1993, 93, 1699-1733;
105. c) B. S. Davisdon, Chem. Rev. 1993, 93, 1771-1791;
106. d) D. J. Faulkner, Nat. Prod. Rep. 1999, 16, 155-198;
107. e) M. C. Bagley, J. W. Dale, E. A. Merrit, X. Xiong, Chem. Rev. 2005, 105, 685-714.
108. a) T. W. Von Geldern, C. Hutchins, J. A. Kester, J. R. Wu-Wong, W. Chiou, D. B. Dixon, T. J. Opgenorth, J. Med. Chem. 1996, 39, 957-967;
109. b) T. W. Von Geldern, J. A. Kester, R. Bal, J. R. Wu-Wong, W. Chiou, D. B. Dixon, T. J. Opgenorth, J. Med. Chem. 1996, 39, 968-981;
110. c) M. Falorni, G. Dettori, G. Giacomelli, Tetrahedron: Asymmetry 1998, 9, 1419-1426;
111. d) M. Falorni, G. Giacomelli, A. Porcheddu, G. Dettori, Eur. J. Org. Chem. 2000, 3217-3222.
112. U. Grabowska, A. Rizzo, K. Farnell, M. Quibell, J. Combi. Chem. 2000, 2, 475-490.
113. a) G. Haberhauer, L. Somogyi, Jr., J. Rebek, Tetrahedron Lett. 2000, 41, 5013-5016;
114. b) L. Somogyi, G. Haberhauer, Jr., J. Rebek, Tetrahedron 2001, 57, 1699;
115. c) Y. Singh, N. Sokolenko, M. J. Kelso, L. R. Gahan, G. Abbenante, D. P. Fairlie, J. Am. Chem. Soc. 2001, 123, 333-334.
116. For recent syntheses, see a) K. S. Cardwell, S. A. Hermitage, A. Sjolin, Tetrahedron Lett. 2000, 41, 4239-4242;
117. b) A. Nishida, M. Fuwa, S. Naruto, Y. Sugano, H. Saito, M. Nakagawa, Tetrahedron Lett. 2000, 41, 4791-4794;
118. c) J. C. Lee, I.-G. Song, Tetrahedron Lett. 2000, 41, 5891-5894;
119. d) J. V. Schaus, J. S. Panck, Org. Lett. 2000, 2, 469-471;
120. e) M. Lautens, A. Roy, Org. Lett. 2000, 2, 555-557;
121. f) A. J. Phillips, Y. Uto, P. Wipf, M. J. Reno, D. R. Williams, Org. Lett. 2000, 2, 1165-1168;
122. g) P. C. Ducept. Synlett 2000, 692-694;
123. h) B. Clapham, C. Spanka, K. D. Janda, Org. Lett. 2001, 3, 2173-2176;
124. i) T. G. M. Dhar, J. Guo, Z. Shen, W. J. Pitts, H. H. Gu, B. C. Chen, R. Zhao, M. S. Bednarz, E. J. Iwanowicz, Org. Lett. 2002, 4, 2091-2093.
125. Total synthesis of representative oxazole-containing natural products: a) D. R. Williams, D. A. Brooks, M. A. Berliner, J. Am. Chem. Soc. 1999, 121, 4924-4925;
126. b) A. B. Smith, G. K. Friestad, J. Barbosa, E. Bertounesque, J. J. W. Duan, K. G. Hull, M. Iwashima, Y. Oiu, P. G. Spoors, B. A. Salvatore, J. Am. Chem. Soc. 1999, 121, 10478-10486;
127. c) S. K. Chattopadhyay, J. Kempson, A. McNeil, G. Pattenden, M. Reader, D. E. Rippon, D. Waite, J. Chem. Soc. 1 2000, 2415-2428;
128. d) S. K. Chattopadhyay, G. Pattenden, J. Chem. Soc. Perkin Trans. 1 2000, 2429-2454;
129. e) M. C. Bagley, K. E. Bashford, C. L. Hesketh, C. J. Moody, J. Am. Chem. Soc. 2000, 122, 3301-3313;
130. f) D. A. Evans, V. J. Cee, T. E. Smith, D. M. Fitch, P. S. Cho, Angew. Chem. 2000, 112, 2633-2636;
131. Angew. Chem. Int. Ed. 2000, 39, 2533-2536;
132. g) D. A. Evans, D. M. Fitch, Angew. Chem. 2000, 112, 2636-2640;
133. Angew. Chem. Int. Ed. 2000, 39, 2536-2540.
134. G. Zhao, C. Bughin, H. Bienaymé, J. Zhu, Synlett 2003, 1153-1154.
135. Acid-catalyzed macrolactonization of ω-hydroxy vinyl ester: B. M. Trost, J. D. Chisholm, Org. Lett. 2002, 4, 3743-3745.
136. B. Oberhauser, K. Baumann, B. Grohmann, H. Sperner, Synlett 1999, 893-896.
137. a) Y. Hitotsuyanagi, S.-I. Sasaki, Y. Matsumoto, K. Yamaguchi, H. Itokawa, K. Takeya, J. Am. Chem. Soc: 2003, 125, 7284-7290;
138. b) Y. Hitotsuyanagi, Y. Matsumoto, S.-I. Sasaki, k. Yamaguchi, H. Itokawa, K. Takeya, Tetrahedron Lett. 2001, 42, 1535-1537.
139. B. M. Trost, Science 1991, 254, 1471-1477.
140. P. A. Wender, S. T. Handy, D. L. Wright, Chem. Ind. 1997, 765-769.
141. W. J. Gottestein, R. B. Babel, L. B. Grast, J. M. Essery, R. R. Fraser, J. C. Godfrey, C. T. Holdrege, W. F. Minor, M. E. Neubert, C. A. Panetta, L. C. Cheney, J. Med. Chem. 1965, 8, 794-797.
142. Elegantly developed site-selective incorporation of thioamide into a peptide based on the azirine/oxazolone method: a) J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1998, 54, 8721-8736;
143. b) J. Lehmann, A. Linden, H. Heimgartner, Tetrahedron 1999, 55, 5359-5376;
144. c) R. Breitenmoser, H. Heimgartner. Helv. Chim. Acta. 2001, 84, 786-796;
145. d) R. Breitenmoser, A. Linden, H. Heimgartner, Helv. Chim. Acta. 2002, 85, 990-991.
146. K. Morokuma, Acc. Chem. Res. 1977, 10, 294-300.
147. For a recent review on conformation-directed macrocyclization, see J. Blankenstein, J. Zhu, Eur. J. Org. Chem. 2005, 1949-1964.
148. S. L. Schreiber, Science 2000, 287, 1964-1969.