SCOPUS 정보 검색 플랫폼

European Journal of Organic Chemistry

Volumn , Issue 12, 2000, Pages 2335-2344

Synthesis of cyclic dipeptides by ring-closing metathesis

(2) Reichwein, John F a Liskamp, Rob M J a

a UTRECHT UNIVERSITY (Netherlands)

Author keywords

Cyclization; Dienes; Metathesis; Peptides; Peptidomimetics; Ring closure

Indexed keywords

PEPTIDE; SOLVENT;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; PEPTIDE SYNTHESIS; REACTION ANALYSIS; RECEPTOR AFFINITY;

EID: 0033937199 PISSN: 1434193X EISSN: None Source Type: Journal
DOI: 10.1002/1099-0690(200006)2000:12<2335::AID-EJOC2335>3.0.CO;2-C Document Type: Article

Times cited : (52)

References (45)

1
- 33745502124
- See e.g.: A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
- (1993) Angew. Chem. , vol.105 , pp. 1303
- Giannis, A.¹ Kolter, T.²

2
- 33745502124
- See e.g.: A. Giannis, T. Kolter, Angew. Chem. 1993, 105, 1303; Angew. Chem. Int. Ed. Engl. 1993, 32, 1244-1267.
- (1993) Angew. Chem. Int. Ed. Engl. , vol.32 , pp. 1244-1267

3
- 0025336463
- See e.g.: V. J. Hruby, F. Al-Obeidi, W. Kazmierski, Biochem. J. 1990, 268, 249-262.
- (1990) Biochem. J. , vol.268 , pp. 249-262
- Hruby, V.J.¹ Al-Obeidi, F.² Kazmierski, W.³

4
- 0026155124
- See e.g.: C. Gilon, D. Halle, M. Chorev, Z. Selinger, G. Byk, Biopolymers 1991, 31, 745-750.
- (1991) Biopolymers , vol.31 , pp. 745-750
- Gilon, C.¹ Halle, D.² Chorev, M.³ Selinger, Z.⁴ Byk, G.⁵

5
- 1542763298
- For recent reviews see: R. H. Grubbs, S. J. Miller, G. C. Fu, Acc, Chem. Res. 1995, 28, 446-452; H.-G. Schmalz, Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Engl. 1995, 34, 1833-1836; R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388; M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
- (1995) Acc, Chem. Res. , vol.28 , pp. 446-452
- Grubbs, R.H.¹ Miller, S.J.² Fu, G.C.³

6
- 0001485244
- For recent reviews see: R. H. Grubbs, S. J. Miller, G. C. Fu, Acc, Chem. Res. 1995, 28, 446-452; H.-G. Schmalz, Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Engl. 1995, 34, 1833-1836; R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388; M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
- (1995) Angew. Chem. , vol.107 , pp. 1981-1984
- Schmalz, H.-G.¹

7
- 33750239613
- For recent reviews see: R. H. Grubbs, S. J. Miller, G. C. Fu, Acc, Chem. Res. 1995, 28, 446-452; H.-G. Schmalz, Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Engl. 1995, 34, 1833-1836; R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388; M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
- (1995) Angew. Chem. Int. Engl. , vol.34 , pp. 1833-1836

8
- 0032580376
- For recent reviews see: R. H. Grubbs, S. J. Miller, G. C. Fu, Acc, Chem. Res. 1995, 28, 446-452; H.-G. Schmalz, Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Engl. 1995, 34, 1833-1836; R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388; M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
- (1998) Tetrahedron , vol.54 , pp. 4413-4450
- Grubbs, R.H.¹ Chang, S.²

9
- 28244440935
- For recent reviews see: R. H. Grubbs, S. J. Miller, G. C. Fu, Acc, Chem. Res. 1995, 28, 446-452; H.-G. Schmalz, Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Engl. 1995, 34, 1833-1836; R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388; M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
- (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 371-388
- Armstrong, S.K.¹

10
- 0000063152
- For recent reviews see: R. H. Grubbs, S. J. Miller, G. C. Fu, Acc, Chem. Res. 1995, 28, 446-452; H.-G. Schmalz, Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Engl. 1995, 34, 1833-1836; R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388; M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
- (1997) Angew. Chem. , vol.109 , pp. 2124-2145
- Schuster, M.¹ Blechert, S.²

11
- 0030771019
- For recent reviews see: R. H. Grubbs, S. J. Miller, G. C. Fu, Acc, Chem. Res. 1995, 28, 446-452; H.-G. Schmalz, Angew. Chem. 1995, 107, 1981-1984; Angew. Chem. Int. Engl. 1995, 34, 1833-1836; R. H. Grubbs, S. Chang, Tetrahedron 1998, 54, 4413-4450; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1 1998, 371-388; M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2145; Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
- (1997) Angew. Chem. Int. Ed. Engl. , vol.36 , pp. 2036-2056

12
- 0032580351
- [5a] A. D. Piscopio, J. F. Miller, K. Koch, Tetrahedron Lett. 1998, 39, 2667-2670; A. D. Piscopio, J. F. Miller, K. Koch, Tetrahedron Lett. 1997, 38, 7143-7146; J. Pernerstorfer, M. Schuster, S. Blechert, Chem. Commun. 1997, 1949-1950.
- (1998) Tetrahedron Lett. , vol.39 , pp. 2667-2670
- Piscopio, A.D.¹ Miller, J.F.² Koch, K.³

13
- 0030693762
- [5a] A. D. Piscopio, J. F. Miller, K. Koch, Tetrahedron Lett. 1998, 39, 2667-2670; A. D. Piscopio, J. F. Miller, K. Koch, Tetrahedron Lett. 1997, 38, 7143-7146; J. Pernerstorfer, M. Schuster, S. Blechert, Chem. Commun. 1997, 1949-1950.
- (1997) Tetrahedron Lett. , vol.38 , pp. 7143-7146
- Piscopio, A.D.¹ Miller, J.F.² Koch, K.³

14
- 0001849406
- [5a] A. D. Piscopio, J. F. Miller, K. Koch, Tetrahedron Lett. 1998, 39, 2667-2670; A. D. Piscopio, J. F. Miller, K. Koch, Tetrahedron Lett. 1997, 38, 7143-7146; J. Pernerstorfer, M. Schuster, S. Blechert, Chem. Commun. 1997, 1949-1950.
- (1997) Chem. Commun. , pp. 1949-1950
- Pernerstorfer, J.¹ Schuster, M.² Blechert, S.³

15
- 0032513726
- [5b] B. E. Fink, P. R. Kym, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1998, 120, 4334-4344; A. S. Ripka, R. S.; Bohacek, D. H. Rich, Bioorg. Med. Chem. Lett. 1998, 8, 357-360; R. H. Grubbs, H. E. Blackwell, Angew. Chem. 1998, 110, 3469-3472; Angew. Chem. Int. Engl. 1998, 37, 3281-3284; T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; E. R. Jarvo, G. T. Copeland, N. Papaioannou, P. J. Bonitatebus, Jr., S. J. Miller, J. Am. Chem. Soc. 1999, 121, 11638-11643.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 4334-4344
- Fink, B.E.¹ Kym, P.R.² Katzenellenbogen, J.A.³

16
- 0032539507
- [5b] B. E. Fink, P. R. Kym, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1998, 120, 4334-4344; A. S. Ripka, R. S.; Bohacek, D. H. Rich, Bioorg. Med. Chem. Lett. 1998, 8, 357-360; R. H. Grubbs, H. E. Blackwell, Angew. Chem. 1998, 110, 3469-3472; Angew. Chem. Int. Engl. 1998, 37, 3281-3284; T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; E. R. Jarvo, G. T. Copeland, N. Papaioannou, P. J. Bonitatebus, Jr., S. J. Miller, J. Am. Chem. Soc. 1999, 121, 11638-11643.
- (1998) Bioorg. Med. Chem. Lett. , vol.8 , pp. 357-360
- Ripka, A.S.¹ Bohacek, R.S.² Rich, D.H.³

17
- 0033596302
- [5b] B. E. Fink, P. R. Kym, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1998, 120, 4334-4344; A. S. Ripka, R. S.; Bohacek, D. H. Rich, Bioorg. Med. Chem. Lett. 1998, 8, 357-360; R. H. Grubbs, H. E. Blackwell, Angew. Chem. 1998, 110, 3469-3472; Angew. Chem. Int. Engl. 1998, 37, 3281-3284; T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; E. R. Jarvo, G. T. Copeland, N. Papaioannou, P. J. Bonitatebus, Jr., S. J. Miller, J. Am. Chem. Soc. 1999, 121, 11638-11643.
- (1998) Angew. Chem. , vol.110 , pp. 3469-3472
- Grubbs, R.H.¹ Blackwell, H.E.²

18
- 0032542374
- [5b] B. E. Fink, P. R. Kym, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1998, 120, 4334-4344; A. S. Ripka, R. S.; Bohacek, D. H. Rich, Bioorg. Med. Chem. Lett. 1998, 8, 357-360; R. H. Grubbs, H. E. Blackwell, Angew. Chem. 1998, 110, 3469-3472; Angew. Chem. Int. Engl. 1998, 37, 3281-3284; T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; E. R. Jarvo, G. T. Copeland, N. Papaioannou, P. J. Bonitatebus, Jr., S. J. Miller, J. Am. Chem. Soc. 1999, 121, 11638-11643.
- (1998) Angew. Chem. Int. Engl. , vol.37 , pp. 3281-3284

19
- 0001073480
- [5b] B. E. Fink, P. R. Kym, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1998, 120, 4334-4344; A. S. Ripka, R. S.; Bohacek, D. H. Rich, Bioorg. Med. Chem. Lett. 1998, 8, 357-360; R. H. Grubbs, H. E. Blackwell, Angew. Chem. 1998, 110, 3469-3472; Angew. Chem. Int. Engl. 1998, 37, 3281-3284; T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; E. R. Jarvo, G. T. Copeland, N. Papaioannou, P. J. Bonitatebus, Jr., S. J. Miller, J. Am. Chem. Soc. 1999, 121, 11638-11643.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 12364-12365
- Clark, T.D.¹ Ghadiri, M.R.²

20
- 0033596302
- [5b] B. E. Fink, P. R. Kym, J. A. Katzenellenbogen, J. Am. Chem. Soc. 1998, 120, 4334-4344; A. S. Ripka, R. S.; Bohacek, D. H. Rich, Bioorg. Med. Chem. Lett. 1998, 8, 357-360; R. H. Grubbs, H. E. Blackwell, Angew. Chem. 1998, 110, 3469-3472; Angew. Chem. Int. Engl. 1998, 37, 3281-3284; T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; E. R. Jarvo, G. T. Copeland, N. Papaioannou, P. J. Bonitatebus, Jr., S. J. Miller, J. Am. Chem. Soc. 1999, 121, 11638-11643.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 11638-11643
- Jarvo, E.R.¹ Copeland, G.T.² Papaioannou, N.³ Bonitatebus Jr., P.J.⁴ Miller, S.J.⁵

21
- 0029860486
- [6a] S. J. Miller, H. E. Blackwell, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 9606-9614.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 9606-9614
- Miller, S.J.¹ Blackwell, H.E.² Grubbs, R.H.³

22
- 0029033474
- [6b] S. J. Miller, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 5855-5856.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 5855-5856
- Miller, S.J.¹ Grubbs, R.H.²

23
- 0032485334
- J. F. Reichwein, R. M. J. Liskamp, Tetrahedron Lett. 1998, 39, 1243-1246.
- (1998) Tetrahedron Lett. , vol.39 , pp. 1243-1246
- Reichwein, J.F.¹ Liskamp, R.M.J.²

24
- 0029146841
- J. A. W. Kruijtzer, R. M. J. Liskamp, Tetrahedron Lett. 1995, 36, 6969-6972: J. A. W. Kruijtzer, L. J. F. Hofmeyer, W. Heerma, C. Versluis, R. M. J. Liskamp, Chem. Eur. J. 1998, 4, 1570-1580.
- (1995) Tetrahedron Lett. , vol.36 , pp. 6969-6972
- Kruijtzer, J.A.W.¹ Liskamp, R.M.J.²

25
- 0031875776
- J. A. W. Kruijtzer, R. M. J. Liskamp, Tetrahedron Lett. 1995, 36, 6969-6972: J. A. W. Kruijtzer, L. J. F. Hofmeyer, W. Heerma, C. Versluis, R. M. J. Liskamp, Chem. Eur. J. 1998, 4, 1570-1580.
- (1998) Chem. Eur. J. , vol.4 , pp. 1570-1580
- Kruijtzer, J.A.W.¹ Hofmeyer, L.J.F.² Heerma, W.³ Versluis, C.⁴ Liskamp, R.M.J.⁵

26
- 0010006234
- T. Pietzonka, D. Seebach, Angew. Chem. 1992, 104, 1543; Angew. Chem. Int. Ed. Engl. 1992, 31, 1481-1482; D. Seebach, O. Bezencon, B. Jaun, T. Pietzonka, J. L. Matthews, F. N. M. Kühnle, B. Schweizer, Helv. Chim. Acta 1996, 79, 588-608.
- (1992) Angew. Chem. , vol.104 , pp. 1543
- Pietzonka, T.¹ Seebach, D.²

27
- 33749139561
- T. Pietzonka, D. Seebach, Angew. Chem. 1992, 104, 1543; Angew. Chem. Int. Ed. Engl. 1992, 31, 1481-1482; D. Seebach, O. Bezencon, B. Jaun, T. Pietzonka, J. L. Matthews, F. N. M. Kühnle, B. Schweizer, Helv. Chim. Acta 1996, 79, 588-608.
- (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 1481-1482

28
- 0000231464
- T. Pietzonka, D. Seebach, Angew. Chem. 1992, 104, 1543; Angew. Chem. Int. Ed. Engl. 1992, 31, 1481-1482; D. Seebach, O. Bezencon, B. Jaun, T. Pietzonka, J. L. Matthews, F. N. M. Kühnle, B. Schweizer, Helv. Chim. Acta 1996, 79, 588-608.
- (1996) Helv. Chim. Acta , vol.79 , pp. 588-608
- Seebach, D.¹ Bezencon, O.² Jaun, B.³ Pietzonka, T.⁴ Matthews, J.L.⁵ Kühnle, F.N.M.⁶ Schweizer, B.⁷

29
- 12944283794
- note
- Abbreviations used: (Nall)Aaa: N-allyl amino acid; (Nhal)Aaa: N-homoallyl amino acid; (Npen)Aaa: N-4-pentenyl amino acid; DCE: 1,2-dichloroethane; TCE: 1,1,2-trichlproethane; DCM: dichloromethane; PyBroP, bromotripyrrolidinophosphonium hexafluorophosphate; TFFH: tetramethylfluoroformamidinium hexafluorophosphate; BOP: (1H-benzotriazol-1-yloxy)tris(dimethyl)phosphonium hexafluorophosphate; HATU: O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate; DiPEA: N,N-diisopropylethylamine; TEA: triethylamine; NMP:1-methyl-2-pyrrolidinone; DEAD: diethylazodicarboxylate; DiAD: diisopropylazodicarboxylate; FmocOSu: N-9-fluorenylmethoxycarbonyloxy)succinimide.

30
- 0001647405
- S. J. Miller, S.-H. Kim, Z.-R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108-2109.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 2108-2109
- Miller, S.J.¹ Kim, S.-H.² Chen, Z.-R.³ Grubbs, R.H.⁴

31
- 12944285249
- note
- Product information from Argonaut Technologies.

32
- 0033582741
- T. R. Hoye, M. A. Promo, Tetrahedron Lett. 1999, 40, 1429-1432.
- (1999) Tetrahedron Lett. , vol.40 , pp. 1429-1432
- Hoye, T.R.¹ Promo, M.A.²

33
- 0041713920
- e.g. S. Krompiec, J. Suwinski, M. Gibas, J. Grobelny, Pol. J. Chem. 1996, 70, 133-134; T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599-2660.
- (1996) Pol. J. Chem. , vol.70 , pp. 133-134
- Krompiec, S.¹ Suwinski, J.² Gibas, M.³ Grobelny, J.⁴

34
- 4244076867
- e.g. S. Krompiec, J. Suwinski, M. Gibas, J. Grobelny, Pol. J. Chem. 1996, 70, 133-134; T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599-2660.
- (1998) Chem. Rev. , vol.98 , pp. 2599-2660
- Naota, T.¹ Takaya, H.² Murahashi, S.-I.³

35
- 0030994105
- E. L. Dias, S. T. Nguyen, R. H. Grubbs, J. Am. Chem. Soc. 1997, 119, 3887-3897.
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 3887-3897
- Dias, E.L.¹ Nguyen, S.T.² Grubbs, R.H.³

36
- 2842617271
- J. J. N. Veerman, J. H. van Maarseveen, G. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Eur. J. Org. Chem. 1998, 2583-2589.
- (1998) Eur. J. Org. Chem. , pp. 2583-2589
- Veerman, J.J.N.¹ Van Maarseveen, J.H.² Visser, G.³ Kruse, C.G.⁴ Schoemaker, H.E.⁵ Hiemstra, H.⁶ Rutjes, F.P.J.T.⁷

37
- 12944267564
- personal communication
- This is a scavenger especially suited for hydride species: R. H. Grubbs, personal communication.
- Grubbs, R.H.¹

38
- 0032566021
- A. K. Ghosh, J. Cappiello, D. Shin, Tetrahedron Lett. 1998, 39, 4651-4654.
- (1998) Tetrahedron Lett. , vol.39 , pp. 4651-4654
- Ghosh, A.K.¹ Cappiello, J.² Shin, D.³

39
- 84989499447
- e.g. D. Seebach, E. Hungerbuhler, R. Naef, P. Schnurrenberger, B. Weidmann, M. Zuger, Synthesis 1982, 138-141.
- (1982) Synthesis , pp. 138-141
- Seebach, D.¹ Hungerbuhler, E.² Naef, R.³ Schnurrenberger, P.⁴ Weidmann, B.⁵ Zuger, M.⁶

40
- 0001627344
- J. F. Reichwein, B. Wels, C. Versluis, J. A. W. Kruijtzer, R. M. J. Liskamp, Angew. Chem. 1999, 111, 3906-3910; Angew. Chem. Int. Ed. 1999, 38, 3684-3687.
- (1999) Angew. Chem. , vol.111 , pp. 3906-3910
- Reichwein, J.F.¹ Wels, B.² Versluis, C.³ Kruijtzer, J.A.W.⁴ Liskamp, R.M.J.⁵

41
- 0033576637
- J. F. Reichwein, B. Wels, C. Versluis, J. A. W. Kruijtzer, R. M. J. Liskamp, Angew. Chem. 1999, 111, 3906-3910; Angew. Chem. Int. Ed. 1999, 38, 3684-3687.
- (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3684-3687

42
- 12944257926
- submitted for publication
- J. F. Reichwein, C. Versluis, R. M. J. Liskamp, submitted for publication.
- Reichwein, J.F.¹ Versluis, C.² Liskamp, R.M.J.³

43
- 0000147695
- E. Arx, M. von Faupel, M. Bruggen, J. Chromatogr. 1976, 120, 224.
- (1976) J. Chromatogr. , vol.120 , pp. 224
- Arx, E.¹ Von Faupel, M.² Bruggen, M.³

44
- 12944271077
- note
- Boc-Phe-Phe-OMe and Boc-Leu-Leu-OMe were prepared by standard peptide synthesis methods.

45
- 45949119318
- P. Sieber, Tetrahedron Lett. 1987, 28, 6147-6150.
- (1987) Tetrahedron Lett. , vol.28 , pp. 6147-6150
- Sieber, P.¹

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.