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Volumn , Issue 8, 2009, Pages 1277-1280

Palladium-catalyzed reaction of arenediazonium tetrafluoroborates with methyl 4-hydroxy-2-butenoate: An approach to 4-aryl butenolides and an expeditious synthesis of rubrolide E

(4) Cacchi, Sandro a Fabrizi, Giancarlo a Goggiamani, Antonella a Sferrazza, Alessio a

a SAPIENZA UNIVERSITY OF ROME (Italy)

Author keywords

Butenolides; Cyclization; Diazonium salts; Heck reaction; Rubrolides

Indexed keywords

4 ARYL BUTENOLIDE; ANTIBIOTIC AGENT; ARENEDIAZONIUM TETRAFLUOROBORATE; BUTENOLIDE; DIAZONIUM COMPOUND; GLYCERYL TRINITRATE; HALOGEN; METHYL 4 HYDROXY 2 BUTENOATE; PALLADIUM; RUBROLIDE E; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG SYNTHESIS; HECK REACTION;

EID: 67649413186 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1088132 Document Type: Article

Times cited : (47)

References (58)

1
- 34249104674
- For an excellent recent review on the palladium chemistry of arenediazonium salts, see
- For an excellent recent review on the palladium chemistry of arenediazonium salts, see: Roglans, A.; Pla-Quintana, A.; Moreno-Mañas, M. Chem. Rev. 2006, 106, 4622.
- (2006) Chem. Rev. , vol.106 , pp. 4622
- Roglans, A.¹ Pla-Quintana, A.² Moreno-Mañas, M.³

2
- 0033957059
- For some recent selected references, see
- For some recent selected references, see: (a) Brunner, H.; Le Cousturier de Courcy, N.; Genêt, J.-P. Synlett 2000, 201.
- (2000) Synlett , pp. 201
- Brunner, H.¹ Le Cousturier De Courcy, N.² Genêt, J.-P.³

3
- 0035603360
- (b) Cai, M. Z.; Hu, R. H.; Zhou, J. Chin. Chem. Lett. 2001, 12, 861.
- (2001) Chin. Chem. Lett. , vol.12 , pp. 861
- Cai, M.Z.¹ Hu, R.H.² Zhou, J.³

4
- 16244369175
- (c) Hu, R.-H.; Liu, X.-L.; Cai, M.-Z. Jiangxi Shifan Daxue Xuebao, Ziran Kexueban 2001, 25, 246;
- (2001) Jiangxi Shifan Daxue Xuebao, Ziran Kexueban , vol.25 , pp. 246
- Hu, R.-H.¹ Liu, X.-L.² Cai, M.-Z.³

5
- 37949045369
- Chem. Abstr. 2001, 136, 355024.
- (2001) Chem. Abstr. , vol.136 , pp. 355024

6
- 0035069374
- (d) Darses, S.; Pucheault, M.; Genêt, J.-P. Eur. J. Org. Chem. 2001, 1121.
- (2001) Eur. J. Org. Chem. , pp. 1121
- Darses, S.¹ Pucheault, M.² Genêt, J.-P.³

7
- 0035804502
- (e) Sengupta, S.; Bhattacharyya, S. Tetrahedron Lett. 2001, 42, 2035.
- (2001) Tetrahedron Lett. , vol.42 , pp. 2035
- Sengupta, S.¹ Bhattacharyya, S.²

8
- 0037071945
- (f) Andrus, M. B.; Song, C.; Zhang, J. Org. Lett. 2002, 4, 2079.
- (2002) Org. Lett. , vol.4 , pp. 2079
- Andrus, M.B.¹ Song, C.² Zhang, J.³

9
- 0037009131
- (g) Selvakumar, K.; Zapf, A.; Spannenberg, A.; Beller, M. Chem. Eur. J. 2002, 8, 3901.
- (2002) Chem. Eur. J. , vol.8 , pp. 3901
- Selvakumar, K.¹ Zapf, A.² Spannenberg, A.³ Beller, M.⁴

10
- 0037049168
- (h) Andrus, M. B.; Ma, Y.; Zang, Y.; Song, C. Tetrahedron Lett. 2002, 43, 9137.
- (2002) Tetrahedron Lett. , vol.43 , pp. 9137
- Andrus, M.B.¹ Ma, Y.² Zang, Y.³ Song, C.⁴

11
- 0346690003
- (i) Ma, Y.; Song, C.; Chai, Q.; Ma, C.; Andrus, M. B. Synthesis 2003, 2886.
- (2003) Synthesis , pp. 2886
- Ma, Y.¹ Song, C.² Chai, Q.³ Ma, C.⁴ Andrus, M.B.⁵

12
- 0037245367
- (j) Wang, C.; Tan, L.-S.; He, J.-P.; Hu, H.-W.; Xu, J.-H. Synth. Commun. 2003, 33, 773.
- (2003) Synth. Commun. , vol.33 , pp. 773
- Wang, C.¹ Tan, L.-S.² He, J.-P.³ Hu, H.-W.⁴ Xu, J.-H.⁵

13
- 0037644428
- (k) Masllorens, J.; Moreno-Mañas, M.; Pla-Quintana, A.; Roglans, A. Org. Lett. 2003, 5, 1559.
- (2003) Org. Lett. , vol.5 , pp. 1559
- Masllorens, J.¹ Moreno-Mañas, M.² Pla-Quintana, A.³ Roglans, A.⁴

14
- 0038639922
- (l) Schmidt, B. Chem. Commun. 2003, 1656.
- (2003) Chem. Commun. , pp. 1656
- Schmidt, B.¹

15
- 10744224290
- (m) Nelson, M. L.; Ismail, M. Y.; McIntyre, L.; Bhatia, B.; Viski, P.; Hawkins, P.; Rennie, G.; Andorsky, D.; Messersmith, D.; Stapleton, K.; Dumornay, J.; Sheahan, P.; Verma, A. K.; Warchol, T.; Levy, S. B. J. Org. Chem. 2003, 68, 5838.
- (2003) J. Org. Chem. , vol.68 , pp. 5838
- Nelson, M.L.¹ Ismail, M.Y.² McIntyre, L.³ Bhatia, B.⁴ Viski, P.⁵ Hawkins, P.⁶ Rennie, G.⁷ Andorsky, D.⁸ Messersmith, D.⁹ Stapleton, K.¹⁰ Dumornay, J.¹¹ Sheahan, P.¹² Verma, A.K.¹³ Warchol, T.¹⁴ Levy, S.B.¹⁵

16
- 0842325286
- (n) Dai, M.; Liang, B.; Wang, C.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 221.
- (2004) Org. Lett. , vol.6 , pp. 221
- Dai, M.¹ Liang, B.² Wang, C.³ Chen, J.⁴ Yang, Z.⁵

17
- 1542298830
- (o) Kabalka, G. W.; Dong, G.; Venkataiah, B. Tetrahedron Lett. 2004, 45, 2775.
- (2004) Tetrahedron Lett. , vol.45 , pp. 2775
- Kabalka, G.W.¹ Dong, G.² Venkataiah, B.³

18
- 16544381080
- (p) Xu, L.-H.; Zhang, Y.-Y.; Wang, X.-L.; Chou, J.-Y. Dyes Pigm. 2004, 62, 283.
- (2004) Dyes Pigm. , vol.62 , pp. 283
- Xu, L.-H.¹ Zhang, Y.-Y.² Wang, X.-L.³ Chou, J.-Y.⁴

19
- 23844511173
- (q) Masllorens, J.; Bouquillon, S.; Roglans, A.; Hénin, F.; Muzart, J. J. Organomet. Chem. 2005, 690, 3822.
- (2005) J. Organomet. Chem. , vol.690 , pp. 3822
- Masllorens, J.¹ Bouquillon, S.² Roglans, A.³ Hénin, F.⁴ Muzart, J.⁵

20
- 34548554297
- (r) Farina, A.; Ferranti, C.; Marra, C.; Guiso, M.; Norcia, G. Nat. Prod. Res. 2007, 21, 564.
- (2007) Nat. Prod. Res. , vol.21 , pp. 564
- Farina, A.¹ Ferranti, C.² Marra, C.³ Guiso, M.⁴ Norcia, G.⁵

21
- 49149104747
- (s) Moro, A. V.; Cardoso, F. S. P.; Correia, C. R. D. Tetrahedron Lett. 2008, 49, 5668.
- (2008) Tetrahedron Lett. , vol.49 , pp. 5668
- Moro, A.V.¹ Cardoso, F.S.P.² Correia, C.R.D.³

22
- 0038662723
- For some recent references, see
- For some recent references, see: (a) Severino, E. A.; Costenaro, E. R.; Garcia, A. L. L.; Correia, C. R. D. Org. Lett. 2003, 5, 305.
- (2003) Org. Lett. , vol.5 , pp. 305
- Severino, E.A.¹ Costenaro, E.R.² Garcia, A.L.L.³ Correia, C.R.D.⁴

23
- 0037450463
- (b) Garcia, A. L. L.; Correia, C. R. D. Tetrahedron Lett. 2003, 44, 1553.
- (2003) Tetrahedron Lett. , vol.44 , pp. 1553
- Garcia, A.L.L.¹ Correia, C.R.D.²

24
- 3242686903
- (c) Montes de Oca, A. C. B.; Correia, C. R. D. ARKIVOC 2003, (x), 390.
- (2003) ARKIVOC , Issue.10 , pp. 390
- Montes De Oca, A.C.B.¹ Correia, C.R.D.²

25
- 0038639922
- (d) Schmidt, B. Chem. Commun. 2003, 1656.
- (2003) Chem. Commun. , pp. 1656
- Schmidt, B.¹

26
- 13244298300
- (e) Garcia Ariel, L. L.; Carpes, M. J. S.; Montes de Oca, A. C. B.; dos Santos, M. A. G.; Santana, C. C.; Correia, C. R. D. J. Org. Chem. 2005, 70, 1050.
- (2005) J. Org. Chem. , vol.70 , pp. 1050
- Garcia Ariel, L.L.¹ Carpes, M.J.S.² Montes De Oca, A.C.B.³ Dos Santos, M.A.G.⁴ Santana, C.C.⁵ Correia, C.R.D.⁶

27
- 3242709955
- (f) Sabino, A. A.; Machado, A. H. L.; Correia, C. R. D.; Eberlin, M. N. Angew. Chem. Int. Ed. 2004, 43, 2514.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 2514
- Sabino, A.A.¹ Machado, A.H.L.² Correia, C.R.D.³ Eberlin, M.N.⁴

28
- 4544382137
- (g) Sabino, A. A.; Machado, A. H. L.; Correia, C. R. D.; Eberlin, M. N. Angew. Chem. Int. Ed. 2004, 43, 4389.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4389
- Sabino, A.A.¹ Machado, A.H.L.² Correia, C.R.D.³ Eberlin, M.N.⁴

29
- 33646459933
- (h) Pastre, J. C.; Correia, C. R. D. Org. Lett. 2006, 8, 1657.
- (2006) Org. Lett. , vol.8 , pp. 1657
- Pastre, J.C.¹ Correia, C.R.D.²

30
- 33751281975
- (i) Burtoloso, A. C. B.; Garcia, A. L. L.; Miranda, K. C.; Correia, C. R. D. Synlett 2006, 3145.
- (2006) Synlett , pp. 3145
- Burtoloso, A.C.B.¹ Garcia, A.L.L.² Miranda, K.C.³ Correia, C.R.D.⁴

31
- 33644690153
- (j) Artuso, E.; Barbero, M.; Degani, I.; Dughera, S.; Fochi, R. Tetrahedron 2006, 62, 3146.
- (2006) Tetrahedron , vol.62 , pp. 3146
- Artuso, E.¹ Barbero, M.² Degani, I.³ Dughera, S.⁴ Fochi, R.⁵

32
- 34547742582
- (k) Meira, P. R. R.; Moro, A. V.; Correia, C. R. D. Synthesis 2007, 2279.
- (2007) Synthesis , pp. 2279
- Meira, P.R.R.¹ Moro, A.V.² Correia, C.R.D.³

33
- 34547196841
- (l) Peixoto da Silva, K.; Godoi, M. N.; Correia, C. R. D. Org. Lett. 2007, 9, 2815.
- (2007) Org. Lett. , vol.9 , pp. 2815
- Peixoto Da Silva, K.¹ Godoi, M.N.² Correia, C.R.D.³

34
- 34250364829
- (m) Barreto, R. de L.; Nascimbem, L. B. L. R.; Correia, C. R. D. Synth. Commun. 2007, 37, 2011.
- (2007) Synth. Commun. , vol.37 , pp. 2011
- De Barreto, R.L.¹ Nascimbem, L.B.L.R.² Correia, C.R.D.³

35
- 54149118754
- (n) Bartoli, G.; Cacchi, S.; Fabrizi, G.; Goggiamani, A. Synlett 2008, 2508.
- (2008) Synlett , pp. 2508
- Bartoli, G.¹ Cacchi, S.² Fabrizi, G.³ Goggiamani, A.⁴

36
- 30944433381
- Perez, R.; Veronese, D.; Coelho, F.; Antunes, O. A. C. Tetrahedron Lett. 2006, 47, 1325.
- (2006) Tetrahedron Lett. , vol.47 , pp. 1325
- Perez, R.¹ Veronese, D.² Coelho, F.³ Antunes, O.A.C.⁴

37
- 33751290719
- Konno, T.; Yamada, S.; Tani, A.; Miyabe, T.; Ishihara, T. Synlett 2006, 3025.
- (2006) Synlett , pp. 3025
- Konno, T.¹ Yamada, S.² Tani, A.³ Miyabe, T.⁴ Ishihara, T.⁵

38
- 44449132297
- Cacchi, S.; Fabrizi, G.; Goggiamani, A.; Persiani, D. Org. Lett. 2008, 10, 1597.
- (2008) Org. Lett. , vol.10 , pp. 1597
- Cacchi, S.¹ Fabrizi, G.² Goggiamani, A.³ Persiani, D.⁴

39
- 1542745282
- Ethyl and methyl 4-hydroxy-2-butenoates were prepared according to literature procedures
- Ethyl and methyl 4-hydroxy-2-butenoates were prepared according to literature procedures: (a) Rambaud, R. Bull. Soc. Chim. Fr. 1934, 1, 1317.
- (1934) Bull. Soc. Chim. Fr. , vol.1 , pp. 1317
- Rambaud, R.¹

40
- 33748825216
- (b) Hassner, A.; Friedman, O.; Dehaen, W. Liebigs Ann./ Recl. 1997, 587.
- (1997) Liebigs Ann./ Recl. , pp. 587
- Hassner, A.¹ Friedman, O.² Dehaen, W.³

41
- 37049088565
- (a) Bezuidenhoudt, B. C. B.; Swanepoel, A.; Brandt, E. V.; Ferreira, D. J. Chem. Soc., Perkin Trans. 1 1990, 2599.
- (1990) J. Chem. Soc., Perkin Trans. 1 , pp. 2599
- Bezuidenhoudt, B.C.B.¹ Swanepoel, A.² Brandt, E.V.³ Ferreira, D.⁴

42
- 0000834770
- (b) Miao, S.; Andersen, R. J. J. Org. Chem. 1991, 56, 6275.
- (1991) J. Org. Chem. , vol.56 , pp. 6275
- Miao, S.¹ Andersen, R.J.²

43
- 0026096863
- (c) Miles, D. H.; Chittawong, V.; Lho, D.-S.; Payne, A. M.; de la Cruz, A. A.; Gomez, E. D.; Weeks, J. A.; Atwood, J. L. J. Nat. Prod. 1991, 54, 286.
- (1991) J. Nat. Prod. , vol.54 , pp. 286
- Miles, D.H.¹ Chittawong, V.² Lho, D.-S.³ Payne, A.M.⁴ De La Cruz, A.A.⁵ Gomez, E.D.⁶ Weeks, J.A.⁷ Atwood, J.L.⁸

44
- 0001500755
- (d) Nohara, T.; Kinjo, J.; Furusawa, J.; Sakai, Y.; Inoue, M.; Shirataki, Y.; Ishibashi, Y.; Yokoe, I.; Komatsu, M. Phytochemistry 1993, 33, 1207.
- (1993) Phytochemistry , vol.33 , pp. 1207
- Nohara, T.¹ Kinjo, J.² Furusawa, J.³ Sakai, Y.⁴ Inoue, M.⁵ Shirataki, Y.⁶ Ishibashi, Y.⁷ Yokoe, I.⁸ Komatsu, M.⁹

45
- 0027844959
- (e) Cerri, A.; Mauri, P.; Mauro, M.; Melloni, P. J. Heterocycl. Chem. 1993, 30, 1581.
- (1993) J. Heterocycl. Chem. , vol.30 , pp. 1581
- Cerri, A.¹ Mauri, P.² Mauro, M.³ Melloni, P.⁴

46
- 0032482530
- (f) Tan, L.; Chen, C.-y.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1998, 39, 3961.
- (1998) Tetrahedron Lett. , vol.39 , pp. 3961
- Tan, L.¹ Chen, C.-Y.² Larsen, R.D.³ Verhoeven, T.R.⁴ Reider, P.J.⁵

47
- 0001310062
- (g) Smith, C. J.; Hettich, R. L.; Jompa, J.; Tahir, A.; Buchanan, M. V.; Ireland, C. M. J. Org. Chem. 1998, 63, 4147.
- (1998) J. Org. Chem. , vol.63 , pp. 4147
- Smith, C.J.¹ Hettich, R.L.² Jompa, J.³ Tahir, A.⁴ Buchanan, M.V.⁵ Ireland, C.M.⁶

48
- 67649403685
- 3): δ = 8.15 (d, J = 8.4 Hz, 2 H), 7.60 (d, J = 8.4 Hz, 2 H), 6.21 (t, J = 1.6 Hz, 2 H), 5.16 (d, J = 1.6 Hz, 2 H), 3.97 (s, 3 H)
- +], 75 (42), 59 (100).

49
- 0000834770
- Miao, S.; Andersen, R. J. J. Org. Chem. 1991, 56, 6275.
- (1991) J. Org. Chem. , vol.56 , pp. 6275
- Miao, S.¹ Andersen, R.J.²

50
- 0034625388
- Ortega, M. J.; Zubia, E.; Ocana, J. M.; Naranjo, S.; Salva, J. Tetrahedron 2000, 56, 3963.
- (2000) Tetrahedron , vol.56 , pp. 3963
- Ortega, M.J.¹ Zubia, E.² Ocana, J.M.³ Naranjo, S.⁴ Salva, J.⁵

51
- 0035842414
- For selected recent syntheses of rubrolides, see
- For selected recent syntheses of rubrolides, see: (a) Bellina, F.; Anselmi, C.; Stephane, V.; Mannina, L.; Rossi, R. Tetrahedron 2001, 57, 9997.
- (2001) Tetrahedron , vol.57 , pp. 9997
- Bellina, F.¹ Anselmi, C.² Stephane, V.³ Mannina, L.⁴ Rossi, R.⁵

52
- 0037060937
- (b) Bellina, F.; Anselmi, C.; Rossi, R. Tetrahedron Lett. 2002, 43, 2023.
- (2002) Tetrahedron Lett. , vol.43 , pp. 2023
- Bellina, F.¹ Anselmi, C.² Rossi, R.³

53
- 0037716269
- (c) Bellina, F.; Anselmi, C.; Manina, F.; Rossi, R. Eur. J. Org. Chem. 2003, 2290.
- (2003) Eur. J. Org. Chem. , pp. 2290
- Bellina, F.¹ Anselmi, C.² Manina, F.³ Rossi, R.⁴

54
- 13844261316
- (d) Boukouvalas, J.; Pouliot, M. Synlett 2005, 343.
- (2005) Synlett , pp. 343
- Boukouvalas, J.¹ Pouliot, M.²

55
- 24944546080
- (e) Kar, A.; Argade, N. P. Synlett 2005, 2284.
- (2005) Synlett , pp. 2284
- Kar, A.¹ Argade, N.P.²

56
- 37049032117
- (f) Chavan, S. P.; Pathak, A. B.; Pandey, A.; Kalkote, U. R. Synth. Commun. 2007, 37, 4253.
- (2007) Synth. Commun. , vol.37 , pp. 4253
- Chavan, S.P.¹ Pathak, A.B.² Pandey, A.³ Kalkote, U.R.⁴

57
- 33845561098
- Doyle, M. P.; Bryker, W. J. J. Org. Chem. 1979, 44, 1572.
- (1979) J. Org. Chem. , vol.44 , pp. 1572
- Doyle, M.P.¹ Bryker, W.J.²

58
- 67649400852
- 2 (5.6 mg, 0.025 mmol) were added, the reaction mixture was warmed at 40°C, and stirred at that temperature for 4 h (the reactor was protected from light with aluminum film)
- 2 [n-hexane-EtOAc, 60:40] to afford 80.0 mg of 3b (73% yield).

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