SCOPUS 정보 검색 플랫폼

Volumn 61, Issue 12, 1996, Pages 3940-3941

Cycloetherification reactions of areneruthenium complexes: Construction of a 16-membered cyclic peptide model for teicoplanin

(4) Pearson, Anthony J a Bignan, Gilles a Zhang, Penglie a Chelliah, Mari a

a CASE WESTERN RESERVE UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; MACROCYCLIC COMPOUND; TEICOPLANIN;

ARTICLE; DRUG SYNTHESIS; MODEL; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029943460 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo960435y Document Type: Article

Times cited : (54)

References (37)

1
- 33845469633
- (a) Reviews: Williams, D. H. Acc. Chem. Res. 1984, 17, 364.
- (1984) Acc. Chem. Res. , vol.17 , pp. 364
- Williams, D.H.¹

2
- 0021154432
- (b) Barna, J. C. J.; Williams, D. H. Ann. Rev. Microbiol. 1984, 38, 339.
- (1984) Ann. Rev. Microbiol. , vol.38 , pp. 339
- Barna, J.C.J.¹ Williams, D.H.²

3
- 0021473287
- (c) Hunt, A. H.; Molloy, R. M.; Occolowitz, J. L.; Marconi, G. G.; Debono, M. J. Am. Chem. Soc. 1984, 106, 4891.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 4891
- Hunt, A.H.¹ Molloy, R.M.² Occolowitz, J.L.³ Marconi, G.G.⁴ Debono, M.⁵

4
- 0021475278
- (d) Barna, J. C. J.; Williams, D. H.; Stone, D. J. M.; Leung, T.-W. C.; Doddrell, D. M. J. Am. Chem. Soc. 1984, 106, 4895.
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 4895
- Barna, J.C.J.¹ Williams, D.H.² Stone, D.J.M.³ Leung, T.-W.C.⁴ Doddrell, D.M.⁵

5
- 0000167756
- Sammes, P. G., Ed.; Wiley: New York
- (e) Bojesen, G. In Topics in Antibiotic Chemistry; Sammes, P. G., Ed.; Wiley: New York, 1980; Vol. 5, p 119.
- (1980) Topics in Antibiotic Chemistry , vol.5 , pp. 119
- Bojesen, G.¹

6
- 0001653722
- Medical Encyclopaedia, Inc.: New York
- (f) Vancomycin was first isolated in 1956 by McCormick et al.: McCormick, M. H.; Stark, W. M.; Pittenger, G. F.; Pittenger, R. C.; McGuire, G. M. Antibiot. Annual 1955-56, Medical Encyclopaedia, Inc.: New York, 1956; p 606.
- (1956) Antibiot. Annual 1955-56 , pp. 606
- McCormick, M.H.¹ Stark, W.M.² Pittenger, G.F.³ Pittenger, R.C.⁴ McGuire, G.M.⁵

7
- 0019786984
- (g) Williamson, M. P.; Williams, D. H. J. Am. Chem. Soc. 1981, 103, 6580.
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 6580
- Williamson, M.P.¹ Williams, D.H.²

8
- 0027401261
- (h) Gerhard, U.; Mackay, J. P.; Maplestone, R. A.; Williams, D. H. J. Am. Chem. Soc. 1993, 115, 232.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 232
- Gerhard, U.¹ Mackay, J.P.² Maplestone, R.A.³ Williams, D.H.⁴

9
- 4243924840
- (i) Rao, A. V. R.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135.
- (1995) Chem. Rev. , vol.95 , pp. 2135
- Rao, A.V.R.¹ Gurjar, M.K.² Reddy, K.L.³ Rao, A.S.⁴

10
- 84942700429
- (a) Williams, D. H.; Williamson, M. P. J. Chem. Soc., Perkin Trans. 1 1985, 949.
- (1985) J. Chem. Soc., Perkin Trans. 1 , pp. 949
- Williams, D.H.¹ Williamson, M.P.²

11
- 0000437775
- (b) Wright G. D.; Walsh, C. T. Acc. Chem. Res. 1992, 25, 468.
- (1992) Acc. Chem. Res. , vol.25 , pp. 468
- Wright, G.D.¹ Walsh, C.T.²

12
- 0027328589
- (c) Walsh, C. T. Science 1993, 261, 308.
- (1993) Science , vol.261 , pp. 308
- Walsh, C.T.¹

13
- 0027942876
- (d) Malabarba A.; Ciabatti R. J. Med. Chem. 1994, 37, 2988. Walsh, C. T.; Fisher, S. L.; Park, J. S.; Prahalad, M.; Wu, Z. Chem. Biol. 1996, 3, 21.
- (1994) J. Med. Chem. , vol.37 , pp. 2988
- Malabarba, A.¹ Ciabatti, R.²

14
- 0029678259
- (d) Malabarba A.; Ciabatti R. J. Med. Chem. 1994, 37, 2988. Walsh, C. T.; Fisher, S. L.; Park, J. S.; Prahalad, M.; Wu, Z. Chem. Biol. 1996, 3, 21.
- (1996) Chem. Biol. , vol.3 , pp. 21
- Walsh, C.T.¹ Fisher, S.L.² Park, J.S.³ Prahalad, M.⁴ Wu, Z.⁵

15
- 0027274921
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 6426
- Evans, D.A.¹ Dinsmore, C.J.² Evrard, D.A.³ DeVries, K.M.⁴

16
- 0025647383
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1990) J. Org. Chem. , vol.55 , pp. 6000
- Boger, D.L.¹ Yohannes, D.²

17
- 0027195552
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1993) J. Org. Chem. , vol.58 , pp. 1425
- Boger, D.L.¹ Nomoto, Y.² Teegarden, B.R.³

18
- 0029044124
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1995) Biorg. Med. Chem. Lett. , vol.5 , pp. 1187
- Boger, D.L.¹ Borzilleri, R.M.²

19
- 0028081032
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1994) Tetrahedron Lett. , vol.35 , pp. 8465
- Rao, A.V.R.¹ Reddy, K.L.² Rao, A.S.³

20
- 85047672006
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1995) Tetrahedron Lett. , vol.36 , pp. 4781
- Bois-Choussy, M.¹ Beugelmans, R.² Bouillon, J.-P.³ Zhu, J.⁴

21
- 0029052791
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1995) Tetrahedron Lett. , vol.36 , pp. 7081
- Zhu, J.¹ Bouillon, J.-P.² Singh, G.P.³ Chastanet, J.⁴ Beugelmans, R.⁵

22
- 0000130499
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1995) J. Org. Chem. , vol.60 , pp. 6389
- Zhu, J.¹ Beugelmans, R.² Bourdet, S.³ Chastanet, J.⁴ Roussi, G.⁵

23
- 0028867282
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1995) Tetrahedron Lett. , vol.36 , pp. 8787
- Beugelmans, R.¹ Neuville, L.² Bois-Choussy, M.³ Zhu, J.⁴

24
- 0028846958
- NAr reactions to construct teicoplanin or vancotnycin models, see: (e) Rao, A. V. R.; Reddy, K. L.; Rao, A. S. Tetrahedron Lett. 1994, 35, 8465. (f) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J.-P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781 (g) Zhu, J.; Bouillon, J.-P.; Singh, G. P.; Chastanet, J.; Beugelmans, R. Tetrahedron Lett. 1995, 36, 7081. (h) Zhu, J.; Beugelmans, R.; Bourdet, S.; Chastanet, J.; Roussi, G. J. Org. Chem. 1995, 60, 6389. (i) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787. (j) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091.
- (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 3091
- Boger, D.L.¹ Borzilleri, R.M.² Nukui, S.³

25
- 0024802535
- Evans, D. A.; Ellman, J. A.; DeVries, K. M. J. Am. Chem. Soc. 1989, 111, 8912.
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 8912
- Evans, D.A.¹ Ellman, J.A.² DeVries, K.M.³

26
- 0024440146
- (a) Suzuki, Y.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1989, 30, 6043.
- (1989) Tetrahedron Lett. , vol.30 , pp. 6043
- Suzuki, Y.¹ Nishiyama, S.² Yamamura, S.³

27
- 0028808151
- (b) Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8621. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8625. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8629. Nakamura, K; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 191.
- (1995) Tetrahedron Lett. , vol.36 , pp. 8621
- Nakamura, K.¹ Nishiyama, S.² Yamamura, S.³

28
- 0028810286
- (b) Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8621. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8625. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8629. Nakamura, K; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 191.
- (1995) Tetrahedron Lett. , vol.36 , pp. 8625
- Nakamura, K.¹ Nishiyama, S.² Yamamura, S.³

29
- 0028808674
- (b) Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8621. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8625. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8629. Nakamura, K; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 191.
- (1995) Tetrahedron Lett. , vol.36 , pp. 8629
- Nakamura, K.¹ Nishiyama, S.² Yamamura, S.³

30
- 0030030207
- (b) Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8621. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8625. Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8629. Nakamura, K; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1996, 37, 191.
- (1996) Tetrahedron Lett. , vol.37 , pp. 191
- Nakamura, K.¹ Nishiyama, S.² Yamamura, S.³

31
- 0026686933
- Chakraborty, T. K.; Reddy, G. V. J. Org. Chem. 1992, 57, 5462.
- (1992) J. Org. Chem. , vol.57 , pp. 5462
- Chakraborty, T.K.¹ Reddy, G.V.²

32
- 0028225225
- Pearson, A. J.; Shin, H. J. Org. Chem. 1994, 59, 2314.
- (1994) J. Org. Chem. , vol.59 , pp. 2314
- Pearson, A.J.¹ Shin, H.²

33
- 0028803941
- (a) Pearson, A. J.; Lee, K. J. Org. Chem. 1995, 60, 7153.
- (1995) J. Org. Chem. , vol.60 , pp. 7153
- Pearson, A.J.¹ Lee, K.²

34
- 15844425599
- Ph.D. Dissertation, Case Western Reserve University
- (b) Lee, K. Ph.D. Dissertation, Case Western Reserve University, 1995.
- (1995)
- Lee, K.¹

35
- 0026572790
- (a) Pearson, A. J.; Park, J. G. J. Org. Chem. 1992, 57, 1744.
- (1992) J. Org. Chem. , vol.57 , pp. 1744
- Pearson, A.J.¹ Park, J.G.²

36
- 37049084209
- (b) Stone, M. J.; Van Dyk, M. S.; Booth, P. M.; Williams, D. H. J. Chem. Soc., Perkin Trans, 1 1991, 1629.
- (1991) J. Chem. Soc., Perkin Trans, 1 , pp. 1629
- Stone, M.J.¹ Van Dyk, M.S.² Booth, P.M.³ Williams, D.H.⁴

37
- 0342987982
- Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1995, 117, 10585.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 10585
- Janetka, J.W.¹ Rich, D.H.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.