Ring-closing metathesis: A powerful tool for the synthesis of simplified salicylihalamide-based V-ATPase inhibitors

Tetrahedron

Volumn 60, Issue 43 SPEC. ISS., 2004, Pages 9635-9647

  Lebreton, Sylvain ^a   Xie, Xiao Song ^b   Ferguson, Deborah ^c   De Brabander, Jef K ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^b UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^c Richardson TX 75081 USA   (United States)

Author keywords

Cancer; Macrocyclic; Natural product; Olefin metathesis; Vacuolar ATPase

Indexed keywords

3 (3 FLUOROPHENYL)PROPYNOIC ACID[3 (4 HYDROXY 5 OXO 8,9,11,14 TETRAHYDRO 5H,7H 6,10 DIOXABENZOCYCLODODECEN 7 YL)PROPENYL]AMIDE; 3 PHENYLPROPYNOIC ACID[3 (4 HYDROXY 5 OXO 8,9,11,14 TETRAHYDRO 5H,7H 6,10 DIOXABENZOCYCLODODECEN 7 YL)PROPENYL]AMIDE; ADENOSINE TRIPHOSPHATASE; ADENOSINE TRIPHOSPHATASE INHIBITOR; ANTINEOPLASTIC AGENT; SALICYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG; [3 (4 HYDROXY 5 OXO 8,9,11,14 TETRAHYDRO 5H,7H 6,10 DIOXABENZOCYCLODODECEN 7 YL)PROPENYL]CARBAMIC ACID BENZYL ESTER; [3 (4 HYDROXY 5 OXO 8,9,11,14 TETRAHYDRO 5H,7H 6,10 DIOXABENZOCYCLODODECEN 7 YL)PROPENYL]CARBAMIC ACID PENTYL ESTER;

ANTINEOPLASTIC ACTIVITY; CANCER GROWTH; CONFERENCE PAPER; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; METHODOLOGY; PRIORITY JOURNAL; RING CLOSING METATHESIS;

EID: 4544286910     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.06.146     Document Type: Conference Paper

References (42)

1. Salicylihalamide: (a) K.L. Erickson, J.A. Beutler, J.H. Cardellina II, and M.R. Boyd J. Org. Chem. 62 1997 8188 8192
2. (b) For a structural revision, see: Y. Wu, L. Esser, and J.K. De Brabander Angew. Chem. Int. Ed. 39 2000 4308 4310
3. and K.L. Erickson, J.A. Beutler, J.H. Cardellina II, and M.R. Boyd J. Org. Chem. 66 2001 1532
4. Lobatamides: (a) T.C. McKee, D.L. Galinis, L.K. Pannell, J.H. Cardellina II, J. Laakso, C.M. Ireland, L. Murray, R.J. Capon, and M.R. Boyd J. Org. Chem. 63 1998 7805 7810
5. (b) Lobatamide A is identical to the structure of YM-75518, see: K.-I. Suzumura, I. Takahashi, H. Matsumoto, K. Nagai, B. Setiawan, R.M. Rantiatmodjo, K.-I. Suzuki, and N. Nagano Tetrahedron Lett. 38 1997 7573 7576
6. Apicularens: R. Jansen, B. Kunze, H. Reichenbach, and G. Höfle Eur. J. Org. Chem. 2000 913 919
7. CJ-12,950 and CJ-13,357: K.A. Dekker, R.J. Aiello, H. Hirai, T. Inagaki, T. Sakakibara, Y. Suzuki, J.F. Thompson, Y. Yamauchi, and N. Kojima J. Antibiot. 51 1998 14 20
8. Oximidines: (a) J.W. Kim, K. Shin-ya, K. Furihata, Y. Hayakawa, and H. Seto J. Org. Chem. 64 1999 153 155
9. Y. Hayakawa, T. Tomikawa, K. Shin-ya, N. Arao, K. Nagai, and K.-I. Suzuki J. Antibiot. 56 2003 899 904
10. Y. Hayakawa, T. Tomikawa, K. Shin-ya, N. Arao, K. Nagai, K.-I. Suzuki, and K. Furihata J. Antibiot. 56 2003 905 908
11. M.R. Boyd, C. Farina, P. Belfiore, S. Gagliardi, J.-W. Kim, Y. Hayakawa, J.A. Beutler, T.C. McKee, B.J. Bowman, and E.J. Bowman J. Pharmacol. Exp. Ther. 297 2001 114 120
12. For an extensive review, see: M. Forgac Adv. Mol. Cell Biol. 1998 403 453
13. For a therapeutic focus, see: C. Farina, and S. Gagliardi Drug Discov. Today 4 1999 163 172
14. For literature prior to 2003, see the following extensive reviews; (a) J.A. Beutler, and T.C. McKee Curr. Med. Chem. 9 2002 1241 1253
15. L. Yet Chem. Rev. 103 2003 4283 4306
16. For more recent literature, see: (a) K.C. Nicolaou, D.W. Kim, R. Baati, A. O'Brate, and P. Giannakakou Chem. Eur. J. 9 2003 6177 6191
17. J.S. Yadav, and P. Srihari Tetrahedron: Asymmetry 15 2004 81 89
18. K. Yang, B. Blackman, W. Diederich, P.T. Flaherty, C.J. Mossman, S. Roy, Y.M. Ahn, and G.I. Georg J. Org. Chem. 68 2003 10030 10039
19. K. Yang, T. Haack, B. Blackman, W.E. Diederich, S. Roy, S. Pusuluri, and G.I. Georg Org. Lett. 5 2003 4007 4009
20. C. Herb, and M.E. Maier J. Org. Chem. 68 2003 8129 8135
21. F. Hilli, J.M. White, and M.A. Rizzacasa Org. Lett. 6 2004 1289 1292
22. Q. Su, and J.S. Panek J. Am. Chem. Soc. 126 2004 2425 2430
23. B.R. Graetz, and S.D. Rychnovsky Org. Lett. 5 2003 3357 3360
24. T. Haack, S. Kurtkaya, J.P. Snyder, and G.I. Georg Org. Lett. 5 2003 5019 5022
25. J.E. Harvey, S.A. Raw, and R.J.K. Taylor Tetrahedron Lett. 44 2003 7209 7212
26. Y. Wu, O.R. Seguil, and J.K. De Brabander Org. Lett. 2 2000 4241 4244
27. Y. Wu, X. Liao, R. Wang, X.-S. Xie, and J.K. De Brabander J. Am. Chem. Soc. 124 2002 3245 3253
28. X.-S. Xie, D. Padron, X. Liao, J. Wang, M.G. Roth, and J.K. De Brabander J. Biol. Chem. 279 2004 19755 19763
29. For analog synthesis related to other members of the family, see Refs. 9b and 10a
30. A.B. Smith III, and J. Zheng Tetrahedron 58 2002 6455 6471
31. (a) Compound 1: A. Fürstner, T. Dierkes, O.R. Thiel, and G. Blanda Chem. Eur. J. 7 2001 5286 5298
32. (b) Compound 2: see Ref. 10c.
33. (c) Compound 3: L. Perez-Serrano, L. Casarrubios, G. Dominguez, P. Gonzalez-Perez, and J. Perez-Castells Synthesis 2002 1810 1812
34. (d) Compound 4: I.N. Houpis Tetrahedron Lett. 32 1991 6675 6678
35. (e) Compound 5: H. Tsukamoto, T. Suzuki, and Y. Kondo Synlett 2003 1105 1108
36. O. Mitsunobu Synthesis 1981 1 28
37. For a comprehensive overview of applications of RCM in organic synthesis, see: Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2.
38. W.C. Lee, and R.H. Grubbs Org. Lett. 2 2000 2145 2147 correction: Org. Lett. 2000, 2, 2559
39. See Ref. 15a and A. Fürstner, O.R. Thiel, and G. Blanda Org. Lett. 2 2000 3731 3734
40. For an excellent illustration of kinetic versus thermodynamic control in RCM reactions to form 10-membered lactones en route to herbarumin and pinolidoxin natural products, see: A. Fürstner, K. Radkowski, C. Wirtz, R. Goddard, C.W. Lehmann, and R. Mynott J. Am. Chem. Soc. 124 2002 7061 7069
41. D.B. Dess, and J.C. Martin J. Am. Chem. Soc. 113 1991 7277 7287
42. For the role of plasmalemmal V-ATPase isoforms in cancer biology, see the following review: S.R. Sennoune, D. Luo, and R. Martinez-Zaguilan Cell Biochem. Biophys. 40 2004 185 206