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Volumn 67, Issue 17, 2002, Pages 6162-6173

Diastereoselective synthesis of new ψ[(E)-CH=CMe]- and ψ[(Z)-CH=CMe]-type alkene dipeptide isosteres by organocopper reagents and application to conformationally restricted cyclic RGD peptidomimetics

(10) Oishi, Shinya a Kamano, Takae a Niida, Ayumu a Odagaki, Yoshihiko b Hamanaka, Nobuyuki b Yamamoto, Mikio c Ajito, Keiichi c Tamamura, Hirokazu a Otaka, Akira a Fujii, Nobutaka a

a KYOTO UNIVERSITY (Japan)

b ONO PHARMACEUTICAL CO (Japan)

c MEIJI SEIKA KAISHA LTD (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOSTERES;

ALKYLATION; AMINO ACIDS; ISOMERS; OLEFINS;

STEREOCHEMISTRY;

ALKENE DERIVATIVE; ARGINYLGLYCYLASPARTIC ACID; COPPER DERIVATIVE; DIPEPTIDE; ALKENE; COPPER; ORGANOMETALLIC COMPOUND; PROLINE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG ACTIVITY; DRUG CONFORMATION; DRUG SYNTHESIS; HUMAN; HUMAN TISSUE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; METHODOLOGY; MOLECULAR MIMICRY; ORGANIC CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; CHEMISTRY, ORGANIC; COPPER; CYCLIZATION; DIPEPTIDES; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PROLINE; STEREOISOMERISM; SUPPORT, NON-U.S. GOV'T;

EID: 0037162666 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo025923m Document Type: Article

Times cited : (57)

References (83)

1
- 0026770377
- (1992) Cell , vol.69 , pp. 11
- Hynes, R.O.¹

2
- 0033858742
- (2000) Biochem. Soc. Trans. , vol.28 , pp. 311
- Humphries, M.J.¹

3
- 0028362876
- (1994) Science , vol.264 , pp. 569
- Brooks, P.C.¹ Clark, R.A.² Cheresh, D.A.³

4
- 0030271574
- (1996) Curr. Opin. Cell Biol. , vol.8 , pp. 724
- Varner, J.A.¹ Cheresh, D.A.²

5
- 0027158885
- (1993) J. Biol. Chem. , vol.268 , pp. 9901
- Ross, F.P.¹ Chappel, J.² Alvarez, J.I.³ Sander, D.⁴ Butler, W.T.⁵ Farach-Carson, M.C.⁶ Mintz, K.A.⁷ Robey, P.G.⁸ Teitelbaum, S.L.⁹ Cheresh, D.A.¹⁰

6
- 0033065782
- (1999) Anticancer Res. , vol.19 , pp. 959
- Kerr, J.S.¹ Wexler, R.S.² Mousa, S.A.³ Robinson, C.S.⁴ Wexler, E.J.⁵ Mohamed, S.⁶ Voss, M.E.⁷ Devenny, J.J.⁸ Czerniak, P.M.⁹ Gudzelak A., Jr.¹⁰ Slee, A.M.¹¹

8
- 0035266184
- (2001) Cancer Res. , vol.61 , pp. 2232
- Kumar, C.C.¹ Malkowski, M.² Yin, Z.³ Tanghetti, E.⁴ Yaremko, B.⁵ Nechuta, T.⁶ Varner, J.⁷ Liu, M.⁸ Smith, E.M.⁹ Neustadt, B.¹⁰ Presta, M.¹¹ Armstrong, L.¹²

10
- 0037186502
- (2002) J. Med. Chem. , vol.45 , pp. 1045
- Goodman, S.L.¹ Hölzemann, G.² Sulyok, G.A.G.³ Kessler, H.⁴

11
- 0025880146
- (1991) FEBS Lett. , vol.291 , pp. 50
- Aumailley, M.¹ Gurrath, M.² Muller, G.³ Calvete, J.⁴ Timpl, R.⁵ Kessler, H.⁶

12
- 0029778085
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 7461
- Haubner, R.¹ Gratias, R.² Diefenbach, B.³ Goodman, S.L.⁴ Jonczyk, A.⁵ Kessler, H.⁶

13
- 0030768536
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 1374
- Haubner, R.¹ Finsinger, D.² Kessler, H.³

14
- 0033549864
- (1999) J. Med. Chem. , vol.42 , pp. 3033
- Dechantsreiter, M.A.¹ Planker, E.² Mathä, B.³ Lohof, E.⁴ Hölzemann, G.⁵ Jonczyk, A.⁶ Goodman, S.L.⁷ Kessler, H.⁸

15
- 0034419296
- (2000) Chem. Soc. Rev. , vol.29 , pp. 119
- Fischer, G.¹

16
- 0000219483
- Peptide secondary structure mimetics
- Symposia-in-print; No. 50
- (1993) Tetrahedron , vol.49 , pp. 3433
- Kahn, M.¹

17
- 0030768259
- (1997) Tetrahedron , vol.53 , pp. 12789
- Hanessian, S.¹ McNaughton-Smith, G.² Lombart, H.-G.³ Lubell, W.D.⁴

18
- 0003857670
- Humana Press, Totowa, New Jersey
- (1999) Peptidomimetics Protocols
- Kazmiersk, W.M.¹

19
- 0033851469
- (2000) Curr. Med. Chem. , vol.7 , pp. 945
- Hruby, V.J.¹ Balse, P.M.²

20
- 0033921872
- (2000) Comb. Chem. High Throughput Screening , vol.3 , pp. 167
- Kim, H.-O.¹ Kahn, M.²

21
- 0037203973
- (2002) J. Med. Chem.. , vol.45 , pp. 541
- Bursavich, M.G.¹ Rich, D.H.²

22
- 0035800352
- (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 2824
- Vasbinder, M.M.¹ Jarvo, E.R.² Miller, S.J.³

23
- 0029139422
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 3280
- Gardner, R.R.¹ Liang, G.-B.² Gellman, S.H.³

24
- 0000428997
- (1998) J. Org. Chem. , vol.63 , pp. 6088
- Wipf, P.¹ Henninger, T.C.² Geib, S.J.³

25
- 0033541110
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 1806
- Gardner, R.R.¹ Liang, G.-B.² Gellman, S.H.³

26
- 0026760304
- (1992) Tetrahedron , vol.48 , pp. 6425
- Bol, K.M.¹ Liskamp, R.M.J.²

27
- 0027164896
- (1993) Tetrahedron Lett. , vol.34 , pp. 5217
- Bohnstedt, A.C.¹ Prasad, J.V.N.V.² Rich, D.H.³

28
- 0027729683
- (1993) J. Org. Chem. , vol.58 , pp. 6609
- Andres, C.J.¹ Macdonald, T.L.² Ocain, T.D.³ Longhi, D.⁴

29
- 0027968473
- (1994) Tetrahedron Lett. , vol.35 , pp. 6033
- Boros, L.G.¹ De Corte, B.² Gimi, R.H.³ Welch, J.T.⁴ Wu, Y.⁵ Handschumacher, R.E.⁶

30
- 0029655675
- (1996) Tetrahedron , vol.52 , pp. 291
- Welch, J.T.¹ Lin, F.²

31
- 0000983397
- (1998) J. Org. Chem. , vol.63 , pp. 7580
- Hart, S.A.¹ Sabat, M.² Etzkorn, F.A.³

32
- 0033617159
- (1999) J. Org. Chem. , vol.64 , pp. 2998
- Hart, S.A.¹ Etzkorn, F.A.²

33
- 0035859316
- (2001) Org. Lett. , vol.3 , pp. 1789
- Hart, S.A.¹ Trindle, C.O.² Etzkorn, F.A.³

34
- 0027658149
- (1993) Bioorg. Med. Chem. , vol.1 , pp. 161
- Shue, Y.-K.¹ Tufano, M.D.² Carrera G.M., Jr.³ Kopecka, H.⁴ Kuyper, S.L.⁵ Holladay, M.W.⁶ Lin, C.W.⁷ Witte, D.G.⁸ Miller, T.R.⁹ Stashko, M.¹⁰ Nadzan, A.M.¹¹

35
- 0027286213
- (1993) Bioorg Med. Chem. Lett. , vol.3 , pp. 1035
- Christos, T.E.¹ Arvanitis, A.² Cain, G.A.³ Johnson, A.L.⁴ Pottorf, R.S.⁵ Tam, S.W.⁶ Schmidt, W.K.⁷

36
- 0028509497
- (1994) Bioorg. Med. Chem. , vol.2 , pp. 939
- Wai, J.S.¹ Bamberger, D.L.² Fisher, T.E.³ Graham, S.L.⁴ Smith, R.L.⁵ Gibbs, J.B.⁶ Mosser, S.D.⁷ Oliff, A.I.⁸ Pompliano, D.L.⁹ Rands, E.¹⁰ Kohl, N.E.¹¹

37
- 0028954769
- (1995) Pancreas , vol.10 , pp. 301
- Wada, M.¹ Doi, R.² Hosotani, R.³ Higashide, S.⁴ Ibuka, T.⁵ Habashita, H.⁶ Nakai, K.⁷ Fujii, N.⁸ Imamura, M.⁹

38
- 0029010769
- (1995) J. Org. Chem. , vol.60 , pp. 3107
- Bartlett, P.A.¹ Otake, A.²

39
- 0030598239
- (1997) Life Sci. , vol.60 , pp. 29
- Fujimoto, K.¹ Doi, R.² Hosotani, R.³ Wada, M.⁴ Lee, J.-U.⁵ Koshiba, T.⁶ Ibuka, T.⁷ Habashita, H.⁸ Nakai, K.⁹ Fujii, N.¹⁰ Imamura, M.¹¹

40
- 0030890678
- (1997) J. Auton. Nerv. Syst. , vol.63 , pp. 179
- Miyasaka, K.¹ Kanai, S.² Masuda, M.³ Ibuka, T.⁴ Nakai, K.⁵ Fujii, N.⁶ Funakoshi, A.⁷

41
- 0035798080
- (2001) Biochem. Biophys. Res. Commun. , vol.288 , pp. 711
- Kawaguchi, M.¹ Hosotani, R.² Ohishi, S.³ Fujii, N.⁴ Tulachan, S.S.⁵ Koizumi, M.⁶ Toyoda, E.⁷ Masui, T.⁸ Nakajima, S.⁹ Tsuji, S.¹⁰ Ida, J.¹¹ Fujimoto, K.¹² Wada, M.¹³ Doi, R.¹⁴ Imamura, M.¹⁵

42
- 18344368807
- (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 923
- Tamamura, H.¹ Hiramatsu, K.² Miyamoto, K.³ Omagari, A.⁴ Oishi, S.⁵ Nakashima, H.⁶ Yamamoto, N.⁷ Kuroda, Y.⁸ Nakagawa, T.⁹ Otaka, A.¹⁰ Fujii, N.¹¹

43
- 33748244110
- (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 801
- Ibuka, T.¹ Habashita, H.² Funakoshi, S.³ Fujii, N.⁴ Oguchi, Y.⁵ Uyehara, T.⁶ Yamamoto, Y.⁷

44
- 0000763199
- (1991) J. Org. Chem. , vol.56 , pp. 4370
- Ibuka, T.¹ Habashita, H.² Otaka, A.³ Fujii, N.⁴ Oguchi, Y.⁵ Uyehara, T.⁶ Yamamoto, Y.⁷

45
- 0026635347
- (1992) Tetrahedron Lett. , vol.33 , pp. 3783
- Ibuka, T.¹ Yoshizawa, H.² Habashita, H.³ Fujii, N.⁴ Chounan, Y.⁵ Tanaka, M.⁶ Yamamoto, Y.⁷

46
- 0030826684
- (1997) Chem. Pharm. Bull. , vol.45 , pp. 1259
- Noda, M.¹ Ibuka, T.² Habashita, H.³ Fujii, N.⁴

47
- 33748237397
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 652
- Ibuka, T.¹ Nakai, K.² Habashita, H.³ Hotta, Y.⁴ Fujii, N.⁵ Mimura, N.⁶ Miwa, Y.⁷ Taga, T.⁸ Yamamoto, Y.⁹

48
- 37049074279
- (1995) J. Chem. Soc., Perkin Trans. 1 , pp. 1359
- Fujii, N.¹ Nakai, K.² Tamamura, H.³ Otaka, A.⁴ Mimura, N.⁵ Miwa, Y.⁶ Taga, T.⁷ Yamamoto, Y.⁸ Ibuka, T.⁹

49
- 0000831199
- (1997) J. Org. Chem. , vol.62 , pp. 2982
- Ibuka, T.¹ Mimura, N.² Ohno, H.³ Nakai, K.⁴ Akaji, M.⁵ Habashita, H.⁶ Tamamura, H.⁷ Miwa, Y.⁸ Taga, T.⁹ Fujii, N.¹⁰ Yamamoto, Y.¹¹

50
- 33751158672
- (1994) J. Org. Chem. , vol.59 , pp. 4875
- Wipf, P.¹ Fritch, P.C.²

51
- 0030977733
- (1997) J. Org. Chem. , vol.62 , pp. 1586
- Wipf, P.¹ Henninger, T.C.²

52
- 0000596010
- (1997) Chem. Commun. , pp. 2327
- Tamamura, H.¹ Yamashita, M.² Muramatsu, H.³ Ohno, H.⁴ Ibuka, T.⁵ Otaka, A.⁶ Fujii, N.⁷

53
- 33746385828
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 2983
- Tamamura, H.¹ Yamashita, M.² Nakajima, Y.³ Sakano, K.⁴ Otaka, A.⁵ Ohno, H.⁶ Ibuka, T.⁷ Fujii, N.⁸

54
- 0034740849
- (2001) J. Chem. Soc. Perkin Trans. 1 , pp. 2445
- Oishi, S.¹ Tamamura, H.² Yamashita, M.³ Odagaki, Y.⁴ Hamanaka, N.⁵ Otaka, A.⁶ Fujii, N.⁷

55
- 0025827481
- (1991) Tetrahedron Lett. , vol.32 , pp. 4969
- Fujii, N.¹ Habashita, H.² Shigemori, N.³ Otaka, A.⁴ Ibuka, T.⁵ Tanaka, M.⁶ Yamamoto, Y.⁷

56
- 0035825087
- (2001) Tetrahedron Lett. , vol.42 , pp. 285
- Otaka, A.¹ Watanabe, H.² Mitsuyama, E.³ Yukimasa, A.⁴ Tamamura, H.⁵ Fujii, N.⁶

57
- 0035817225
- (2001) Tetrahedron Lett. , vol.42 , pp. 5443
- Otaka, A.¹ Watanabe, H.² Yukimasa, A.³ Oishi, S.⁴ Tamamura, H.⁵ Fujii, N.⁶

58
- 0037018473
- (2002) Org. Lett. , vol.4 , pp. 1055
- Oishi, S.¹ Niida, A.² Kamano, T.³ Odagaki, Y.⁴ Tamamura, H.⁵ Otaka, A.⁶ Hamanaka, N.⁷ Fujii, N.⁸

59
- 0030902124
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 186
- Krause, N.¹ Gerold, A.²

60
- 0037018476
- (2002) Org. Lett. , vol.4 , pp. 1051
- Oishi, S.¹ Kamano, T.² Niida, A.³ Odagaki, Y.⁴ Tamamura, H.⁵ Otaka, A.⁶ Hamanaka, N.⁷ Fujii, N.⁸

61
- 0000476716
- (1984) Tetrahedron Lett. , vol.25 , pp. 2183
- Blanchette, M.A.¹ Choy, W.² Davis, J.T.³ Essenfeld, A.P.⁴ Masamune, S.⁵ Roush, W.R.⁶ Sakai, T.⁷

62
- 0023907011
- (1988) Tetrahedron , vol.44 , pp. 805
- Yajima, H.¹ Fujii, N.² Funakoshi, S.³ Watanabe, T.⁴ Murayama, E.⁵ Otaka, A.⁶

63
- 0000830285
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 1899
- Mitchell, H.J.¹ Nelson, A.² Warren, S.³

64
- 0037154749
- (2002) J. Org. Chem. , vol.67 , pp. 1045
- Hoffman, R.V.¹ Maslouh, N.² Cervantes-Lee, F.³

65
- 0026594555
- (1992) Tetrahedron Lett. , vol.33 , pp. 2031
- Tohdo, K.¹ Hamada, Y.² Shoiri, T.³

66
- 0033588064
- (1999) Tetrahedron Lett. , vol.40 , pp. 6163
- Wasserman, H.H.¹ Xia, M.² Petersen, A.K.³ Jorgensen, M.R.⁴ Curtis, E.A.⁵

67
- 0035940114
- (2001) Org. Lett. , vol.3 , pp. 2725
- Travins, J.M.¹ Bursavich, M.G.² Veber, D.F.³ Rich, D.H.⁴

68
- 0031437464
- (1997) J. Org. Chem. , vol.62 , pp. 9348
- Benedetti, F.¹ Miertus, S.² Norbedo, S.³ Tossi, A.⁴ Zlatoidzky, P.⁵

69
- 0033534699
- (1999) J. Org Chem. , vol.64 , pp. 242
- Yang, H.¹ Sheng, X.C.² Harrington, E.M.³ Ackermann, K.⁴ Garcia, A.M.⁵ Lewis, M.D.⁶

70
- 2142860505
- note

71
- 0000067854
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 4864
- Ibuka, T.¹ Tanaka, M.² Nishii, S.³ Yamamoto, Y.⁴

72
- 0000788563
- (1989) J. Org. Chem. , vol.54 , pp. 4055
- Ibuka, T.¹ Akimoto, N.² Tanaka, M.³ Nishii, S.⁴ Yamamoto, Y.⁵

73
- 2142802376
- note

74
- 2142745099
- (1990) Tetrahedron: Asymmetry , vol.1 , pp. 379
- Ibuka, T.¹ Habashita, H.² Funakoshi, S.³ Fujii, N.⁴ Baba, K.⁵ Kozawa, M.⁶ Oguchi, Y.⁷ Uyehara, T.⁸ Yamamoto, Y.⁹

75
- 2142861014
- note

76
- 0000214553
- (1961) Collect. Czech. Chem. Commun. , vol.26 , pp. 2333
- Honzl, J.¹ Rudinger, J.²

77
- 2142744581
- note

78
- 0024359592
- (1989) Tetrahedron Lett. , vol.30 , pp. 3943
- Barlos, K.¹ Gatos, D.² Kallitsis, J.³ Papaphotiu, G.⁴ Sotiriu, P.⁵ Wenqing, Y.⁶ Schäfer, W.⁷

79
- 0024381307
- (1989) Tetrahedron Lett. , vol.30 , pp. 3947
- Barlos, K.¹ Gatos, D.² Kapolos, S.³ Papaphotiu, G.⁴ Schäfer, W.⁵ Wenqing, Y.⁶

80
- 0026338002
- (1991) Int. J. Pept. Protein Res. , vol.38 , pp. 555
- Barlos, K.¹ Gatos, D.² Kapolos, S.³ Poulos, C.⁴ Schäfer, W.⁵ Wenqing, Y.⁶

81
- 0016205435
- (1974) Chem. Pharm. Bull. , vol.22 , pp. 855
- Shioiri, T.¹ Yamada, S.²

82
- 0023087267
- (1987) Methods Enzymol. , vol.144 , pp. 475
- Pytela, R.¹ Pierschbacher, M.D.² Argraves, S.³ Suzuki, S.⁴ Rouslahti, E.⁵

83
- 0026482439
- (1992) Blood , vol.80 , pp. 2539
- Kouns, W.C.¹ Kirchhofer, D.² Hadvary, P.³ Edenhofer, A.⁴ Weller, T.⁵ Pfenninger, G.⁶ Baumgartner, H.R.⁷ Jennings, L.K.⁸ Steiner, B.⁹

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