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Volumn 25, Issue 5-6, 2006, Pages 519-526

Rapid synthesis of cyclopeptide alkaloid-like para-cyclophanes by combined use of Ugi-4CR and intramolecular SNAr reaction

(3) Cristau, Pierre a,b Vors, Jean Pierre b Zhu, Jieping a

a CNRS (France)

b BAYER AG (Germany)

Author keywords

Cyclopeptide alkaloid; Intramolecular SNAr rection; Macrocyclization; Multicomponent reaction; Natural product like; Ugi 4CR

Indexed keywords

METABOLITES; NITROGEN COMPOUNDS; SULFUR COMPOUNDS;

CYCLOPEPTIDE ALKALOID; CYCLOPEPTIDES; INTRAMOLECULAR SNAR RECTION; MACRO-CYCLIZATION; MULTICOMPONENT REACTION; MULTICOMPONENTS; NATURAL PRODUCT-LIKE; NATURAL PRODUCTS; RAPID SYNTHESIS; UGI-4CR;

ALKALOIDS;

ALDEHYDE; ALKALOID; CARBOXYLIC ACID; CYCLOPEPTIDE; CYCLOPHANE DERIVATIVE; ISONITRILE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 33745783494 PISSN: 1611020X EISSN: 16110218 Source Type: Journal
DOI: 10.1002/qsar.200540214 Document Type: Article

Times cited : (27)

References (38)

1
- 77957096122
- A. Brassi (Ed.), Academic Press, New York
- For reviews, see: a) U. Schmidt, A. Lieberknecht, E. Haslinger, in: A. Brassi (Ed.), The Alkaloids, Vol. 26, Academic Press, New York, 1985, pp. 299-326;
- (1985) The Alkaloids , vol.26 , pp. 299-326
- Schmidt, U.¹ Lieberknecht, A.² Haslinger, E.³

2
- 0003870273
- S. W. Pelletier (Ed.), Wiley, New York
- b) M. M. Joullié, R. F. Nutt, in: S. W. Pelletier (Ed.), Alkaloids: Chemical and Biological Perspectives, Vol. 3, Wiley, New York, 1985, pp. 113-168;
- (1985) Alkaloids: Chemical and Biological Perspectives , vol.3 , pp. 113-168
- Joullié, M.M.¹ Nutt, R.F.²

3
- 0030912795
- c) D. C. Gournelis, G. G. Laskaris, R. Verpoorte, Nat. Prod. Rep. 1997, 75-82.
- (1997) Nat. Prod. Rep. , pp. 75-82
- Gournelis, D.C.¹ Laskaris, G.G.² Verpoorte, R.³

4
- 6344258480
- For a recent overview, see: a) M. Joullié, D. J. Richard, Chem. Commun. 2004, 2011-2015.
- (2004) Chem. Commun. , pp. 2011-2015
- Joullié, M.¹ Richard, D.J.²

5
- 18444389766
- and references cited therein
- For recent total syntheses of mauritines A, B, C and F, see: 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 cited therein.
- (2005) Chem. Eur. J. , vol.11 , pp. 2668-2679
- Cristau, P.¹ Temal-Laïb, T.² Bois-Choussy, M.³ Martin, M.T.⁴ Vors, J.P.⁵ Zhu, J.⁶

6
- 0034699496
- J. D. A. Tyndall, R. C. Reid, D. P. Tyssen, D. K. Jardine, B. Todd, M. Passmore, D. R. March, L. K. Pattenden, D. A. Bergman, D. Alewood, S.-H. Hu, P. F. Alewood, C. J. Birch, J. L. Martin, D. P. Fairlie, J. Med. Chem. 2000, 43, 3495-3504.
- (2000) J. Med. Chem. , vol.43 , pp. 3495-3504
- Tyndall, J.D.A.¹ Reid, R.C.² Tyssen, D.P.³ Jardine, D.K.⁴ Todd, B.⁵ Passmore, M.⁶ March, D.R.⁷ Pattenden, L.K.⁸ Bergman, D.A.⁹ Alewood, D.¹⁰ Hu, S.-H.¹¹ Alewood, P.F.¹² Birch, C.J.¹³ Martin, J.L.¹⁴ Fairlie, D.P.¹⁵

7
- 0032725569
- Y. Feng, K. Burgess, Chem. Eur. J. 1999, 5, 3261-3272.
- (1999) Chem. Eur. J. , vol.5 , pp. 3261-3272
- Feng, Y.¹ Burgess, K.²

8
- 0033518049
- C. W. West, D. H. Rich, Org. Lett. 1999, 1, 1819-1822.
- (1999) Org. Lett. , vol.1 , pp. 1819-1822
- West, C.W.¹ Rich, D.H.²

9
- 0029084673
- D. P. Fairlie, G. Abbenante, D. R. March, Curr. Med. Chem. 1995, 2, 654-686.
- (1995) Curr. Med. Chem. , vol.2 , pp. 654-686
- Fairlie, D.P.¹ Abbenante, G.² March, D.R.³

10
- 1542527790
- a) J. Zhu, Synlett 1997, 133-144;
- (1997) Synlett , pp. 133-144
- Zhu, J.¹

11
- 0342757538
- b) J. S. Sawyer, Tetrahedron 2000, 56, 5045-5065;
- (2000) Tetrahedron , vol.56 , pp. 5045-5065
- Sawyer, J.S.¹

12
- 0037196315
- c) T. Temal-Laïb, J. Chastanet, J. Zhu, J. Am. Chem. Soc. 2002, 124, 583-590;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 583-590
- Temal-Laïb, T.¹ Chastanet, J.² Zhu, J.³

13
- 18444389766
- d) P. Cristau, T. Temal-Laïb, M. Bois-Choussy, M. T. Martin, J. P. Vors, J. Zhu, Chem. Eur. J. 2005, 11, 2668-2679.
- (2005) Chem. Eur. J. , vol.11 , pp. 2668-2679
- Cristau, P.¹ Temal-Laïb, T.² Bois-Choussy, M.³ Martin, M.T.⁴ Vors, J.P.⁵ Zhu, J.⁶

14
- 84890574887
- : J. Zhu, H. Bienaymé (Eds.), Wiley-VCH, Weinheim
- S. Marcaccini, T. Torroba, in: J. Zhu, H. Bienaymé (Eds.), Post-condensation Modifications of the Passerini and Ugi Reactions, Wiley-VCH, Weinheim, 2005, pp. 33-75.
- (2005) Post-condensation Modifications of the Passerini and Ugi Reactions , pp. 33-75
- Marcaccini, S.¹ Torroba, T.²

15
- 8744279305
- L. A. Wessjohann, E. Ruijter, Top. Curr. Chem. 2005, 243, 137-184.
- (2005) Top. Curr. Chem. , vol.243 , pp. 137-184
- Wessjohann, L.A.¹ Ruijter, E.²

16
- 11444270745
- R. Gámez-Montaño, J. Zhu, J. Chem. Soc., Chem. Commun. 2002, 2448-2449.
- (2002) J. Chem. Soc., Chem. Commun. , pp. 2448-2449
- Gámez-Montaño, R.¹ Zhu, J.²

17
- 0035856895
- a) P. Cristau, J. P. Vors, Zhu, J. Org. Lett. 2001, 3, 4079-4082;
- (2001) Org. Lett. , vol.3 , pp. 4079-4082
- Cristau, P.¹ Vors, J.P.² Zhu, J.³

18
- 0037492348
- b) P. Cristau, J. P. Vors, Zhu, J. Tetrahedron Lett. 2003, 44, 5575-5578;
- (2003) Tetrahedron Lett. , vol.44 , pp. 5575-5578
- Cristau, P.¹ Vors, J.P.² Zhu, J.³

19
- 0141852318
- c) P. Cristau, J. P. Vors, Zhu, J. Tetrahedron 2003, 59, 7859-7870.
- (2003) Tetrahedron , vol.59 , pp. 7859-7870
- Cristau, P.¹ Vors, J.P.² Zhu, J.³

20
- 0035939470
- P. Tempest, V. Ma, M. G. Kelly, W. Jones, C. Hulme, Tetrahedron Lett. 2001, 42, 4963-4968;
- (2001) Tetrahedron Lett. , vol.42 , pp. 4963-4968
- Tempest, P.¹ Ma, V.² Kelly, M.G.³ Jones, W.⁴ Hulme, C.⁵

21
- 0037463502
- b) P. Tempest, L. Pettus, V. Gore, C. Hulme, Tetrahedron Lett. 2003, 44, 1947-1950.
- (2003) Tetrahedron Lett. , vol.44 , pp. 1947-1950
- Tempest, P.¹ Pettus, L.² Gore, V.³ Hulme, C.⁴

22
- 0034665244
- For recent reviews, see: a) H. Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321-3329;
- (2000) Chem. Eur. J. , vol.6 , pp. 3321-3329
- Bienaymé, H.¹ Hulme, C.² Oddon, G.³ Schmitt, P.⁴

23
- 0037238724
- b) C. Hulme, V. Gore, Curr. Med. Chem. 2003, 10, 51-80;
- (2003) Curr. Med. Chem. , vol.10 , pp. 51-80
- Hulme, C.¹ Gore, V.²

24
- 0042745386
- c) R. V. A. Orru, M. De Greef, Synthesis 2003, 1471-1499;
- (2003) Synthesis , pp. 1471-1499
- Orru, R.V.A.¹ De Greef, M.²

25
- 0141757224
- d) A. Jacobi von Wangelin, H. Neumann, D. Gördes, S. Klaus, D. Strübing, M. Beller, Chem. Eur. J. 2003, 9, 4286-4294;
- (2003) Chem. Eur. J. , vol.9 , pp. 4286-4294
- Von Jacobi Wangelin, A.¹ Neumann, H.² Gördes, D.³ Klaus, S.⁴ Strübing, D.⁵ Beller, M.⁶

26
- 0348147693
- e) V. Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth, J. S. Mathen, L. Balagopal, Acc. Chem. Res. 2003, 36, 899-907;
- (2003) Acc. Chem. Res. , vol.36 , pp. 899-907
- Nair, V.¹ Rajesh, C.² Vinod, A.U.³ Bindu, S.⁴ Sreekanth, A.R.⁵ Mathen, J.S.⁶ Balagopal, L.⁷

27
- 0037391570
- f) J. Zhu, Eur. J. Org. Chem. 2003, 1133-1144;
- (2003) Eur. J. Org. Chem. , pp. 1133-1144
- Zhu, J.¹

28
- 0242595741
- g) G. Balme, E. Bossharth, N. Monteiro, Eur. J. Org. Chem. 2003, 4101-4111;
- (2003) Eur. J. Org. Chem. , pp. 4101-4111
- Balme, G.¹ Bossharth, E.² Monteiro, N.³

29
- 0037450058
- h) M. Murakami, Angew. Chem. Int. Ed. 2003, 42, 718-720;
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 718-720
- Murakami, M.¹

30
- 11144310072
- i) C. Simon, T. Constantieux, J. Rodriguez, Eur. J. Org. Chem. 2004, 4957-4980;
- (2004) Eur. J. Org. Chem. , pp. 4957-4980
- Simon, C.¹ Constantieux, T.² Rodriguez, J.³

31
- 31544434530
- j) A. Dömling, Chem. Rev. 2006, 106, 17-89.
- (2006) Chem. Rev. , vol.106 , pp. 17-89
- Dömling, A.¹

32
- 85192504749
- in press (private communication)
- M. de Greef, S. Abeln, K. Belkasmi, A. Dömling, R. V. A. Orru, L. A. Wessjohann, Synthesis, in press (private communication).
- Synthesis
- De Greef, M.¹ Abeln, S.² Belkasmi, K.³ Dömling, A.⁴ Orru, R.V.A.⁵ Wessjohann, L.A.⁶

33
- 0037139571
- For other related MCRs promoted by ammonium chloride, see: a) P. Janvier, X. Sun, H. Bienaymé, J. Zhu, J. Am. Chem. Soc. 2002, 124, 2560-2567;
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 2560-2567
- Janvier, P.¹ Sun, X.² Bienaymé, H.³ Zhu, J.⁴

34
- 0037020334
- b) A. Fayol, J. Zhu, Angew. Chem. Int. Ed. 2002, 41, 3633-3635;
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3633-3635
- Fayol, A.¹ Zhu, J.²

35
- 0742304175
- c) A. Fayol, J. Zhu, Org. Lett. 2004, 6, 115-118;
- (2004) Org. Lett. , vol.6 , pp. 115-118
- Fayol, A.¹ Zhu, J.²

36
- 28244443389
- d) D. Bonne, M. Dekhane, J. Zhu, Org. Lett. 2005, 7, 5285-5288.
- (2005) Org. Lett. , vol.7 , pp. 5285-5288
- Bonne, D.¹ Dekhane, M.² Zhu, J.³

37
- 85192505368
- note
- Synthesis of 10b was detailed in reference 12c.

38
- 26844537872
- A. B. Charette (Ed.), John Wiley & Sons Inc.
- L. Banfi, R. Riva, in: A. B. Charette (Ed.), Organic Reactions, Vol. 65, John Wiley & Sons Inc., 2005, pp. 1-140.
- (2005) Organic Reactions , vol.65 , pp. 1-140
- Banfi, L.¹ Riva, R.²

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