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Volumn 4, Issue 8, 2007, Pages 553-555

Total synthesis of (±)-euryfuran through Ti(III) catalyzed radical cyclization

(5) Rosales, Antonio a López Sánchez, Cristóbal a Alvarez Corral, Miriam a Muñoz Dorado, Manuel a Rodríguez García, Ignacio a

a UNIVERSITY OF ALMERÍA (Spain)

Author keywords

Cyclization; Diastereoselectivity; Farnesol; Furanosesquiterpenes; Radical reactions; Titanium

Indexed keywords

EID: 38049121184 PISSN: 15701786 EISSN: None Source Type: Journal
DOI: 10.2174/157017807782795457 Document Type: Article

Times cited : (11)

References (44)

1
- 33746337304
- Gross, H.; Konig, G.M. Phytochem. Rev., 2006, 5, 115.
- (2006) Phytochem. Rev , vol.5 , pp. 115
- Gross, H.¹ Konig, G.M.²

2
- 33746498355
- Liu, Y.H.; Zhang, S.; Abreu, P.J.M. Nat. Prod. Rep., 2006, 23, 630.
- (2006) Nat. Prod. Rep , vol.23 , pp. 630
- Liu, Y.H.¹ Zhang, S.² Abreu, P.J.M.³

3
- 33644973407
- Blunt, J.W.; Copp, B.R.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R. Nat. Prod. Rep., 2006, 23, 26.
- (2006) Nat. Prod. Rep , vol.23 , pp. 26
- Blunt, J.W.¹ Copp, B.R.² Munro, M.H.G.³ Northcote, P.T.⁴ Prinsep, M.R.⁵

4
- 84889865831
- Springer: New York
- Bhakuni, D. S.; Verma, R. Bioactive Marine Natural Products; Springer: New York, 2005.
- (2005) Bioactive Marine Natural Products
- Bhakuni, D.S.¹ Verma, R.²

5
- 0001943337
- Hochlowski, J.E.; Walker, R.P.; Ireland, C.; Faulkner, D.J. J. Org. Chem., 1982, 47, 88.
- (1982) J. Org. Chem , vol.47 , pp. 88
- Hochlowski, J.E.¹ Walker, R.P.² Ireland, C.³ Faulkner, D.J.⁴

6
- 0002287488
- Dunlop, R.W.; Kazlauskas, R.; March, G.; Murphy, P.T.; Wells, R.J. Aust. J. Chem., 1982, 35, 95.
- (1982) Aust. J. Chem , vol.35 , pp. 95
- Dunlop, R.W.¹ Kazlauskas, R.² March, G.³ Murphy, P.T.⁴ Wells, R.J.⁵

7
- 26844478719
- Gaspar, H.; Gavagnin, M.; Calado, G.; Castelluccio, F.; Mollo, E.; Cimino, G. Tetrahedron, 2005, 61, 11032.
- (2005) Tetrahedron , vol.61 , pp. 11032
- Gaspar, H.¹ Gavagnin, M.² Calado, G.³ Castelluccio, F.⁴ Mollo, E.⁵ Cimino, G.⁶

8
- 24144501312
- Hellio, C.; Tsoukatou, M.; Marechal, J.P.; Aldred, N.; Beaupoil, C.; Clare, A.S.; Vagias, C.; Roussis, V. Marine Blotechnology, 2005, 55, 297.
- (2005) Marine Blotechnology , vol.55 , pp. 297
- Hellio, C.¹ Tsoukatou, M.² Marechal, J.P.³ Aldred, N.⁴ Beaupoil, C.⁵ Clare, A.S.⁶ Vagias, C.⁷ Roussis, V.⁸

9
- 0026691647
- Gulavita, N.K.; Gunasekera, S.P.; Pomponi, S.A. J. Nat. Prod., 1992, 55, 506.
- (1992) J. Nat. Prod , vol.55 , pp. 506
- Gulavita, N.K.¹ Gunasekera, S.P.² Pomponi, S.A.³

10
- 0037185444
- Valderrama, J.A.; Benites, J.; Cortes, M.; Pessoa-Mahana, D.; Prina, E.; Fournet, A. Tetrahedron, 2002, 58, 881.
- (2002) Tetrahedron , vol.58 , pp. 881
- Valderrama, J.A.¹ Benites, J.² Cortes, M.³ Pessoa-Mahana, D.⁴ Prina, E.⁵ Fournet, A.⁶

11
- 0141957599
- VaIderrama, J.A.; Benites, J.; Cortes, M.; Pessoa-Mahana, H.; Prins, E.; Fournet, A. Bioorg. Med. Chem., 2003, 11, 4713.
- (2003) Bioorg. Med. Chem , vol.11 , pp. 4713
- VaIderrama, J.A.¹ Benites, J.² Cortes, M.³ Pessoa-Mahana, H.⁴ Prins, E.⁵ Fournet, A.⁶

12
- 84984187717
- Capelle, N.; Braekman, J.C.; Daloze, D.; Tursch, B. Bull. Soc., Chim. Belg., 1980, 89, 399.
- (1980) Bull. Soc., Chim. Belg , vol.89 , pp. 399
- Capelle, N.¹ Braekman, J.C.² Daloze, D.³ Tursch, B.⁴

13
- 0036178793
- Betancur-Galvis, L.; Zuluaga, C.; Amo, M.; Gonzalez, M.A.; Zaragoza, R.J. J. Nat. Prod., 2002, 65, 189.
- (2002) J. Nat. Prod , vol.65 , pp. 189
- Betancur-Galvis, L.¹ Zuluaga, C.² Amo, M.³ Gonzalez, M.A.⁴ Zaragoza, R.J.⁵

14
- 0028279656
- Baba, Y.; Sakamoto, T.; Soejima, S.; Kanematsu, K. Tetrahedron, 1994, 50, 5645.
- (1994) Tetrahedron , vol.50 , pp. 5645
- Baba, Y.¹ Sakamoto, T.² Soejima, S.³ Kanematsu, K.⁴

15
- 0008149927
- Jansen, B.J.M.; Peperzak, R.M.; De Groot, A. Recl. Trav. Chim. Pays-Bas., 1987, 106, 549.
- (1987) Recl. Trav. Chim. Pays-Bas , vol.106 , pp. 549
- Jansen, B.J.M.¹ Peperzak, R.M.² De Groot, A.³

16
- 0001295782
- Kanematsu, K.; Soejima, S. Heterocycles, 1991, 32, 1483.
- (1991) Heterocycles , vol.32 , pp. 1483
- Kanematsu, K.¹ Soejima, S.²

17
- 0004781895
- Ley, S.V.; Mahon, M. J. Chem. Soc. Perkin Trans. I, 1983,1379.
- (1983) J. Chem. Soc. Perkin Trans. I , pp. 1379
- Ley, S.V.¹ Mahon, M.²

18
- 0008017398
- Cortes, M.; Razmilic, I.; Lopez, J. Bull. Soc. Chim. BeIg., 1987, 96, 631.
- (1987) Bull. Soc. Chim. BeIg , vol.96 , pp. 631
- Cortes, M.¹ Razmilic, I.² Lopez, J.³

19
- 37049068573
- Nakano, T.; Maillo, M.A.; Rojas, A. J. Chem. Soc. Perkin Trans. I, 1987, 2137.
- (1987) J. Chem. Soc. Perkin Trans. I , pp. 2137
- Nakano, T.¹ Maillo, M.A.² Rojas, A.³

20
- 2542616938
- Nakano, T.; Villamizar, J.; Maillo, M.A. J. Chem. Res. Synop., 1998, 560.
- (1998) J. Chem. Res. Synop , pp. 560
- Nakano, T.¹ Villamizar, J.² Maillo, M.A.³

21
- 0010676662
- Villarnizar, J. Rev. Latinoam. Quim., 1999, 27, 96.
- (1999) Rev. Latinoam. Quim , vol.27 , pp. 96
- Villarnizar, J.¹

22
- 33845280764
- Nugent, W.A.; Rajanbabu, T.V. J. Am. Chem. Soc., 1988, 110, 8561.
- (1988) J. Am. Chem. Soc , vol.110 , pp. 8561
- Nugent, W.A.¹ Rajanbabu, T.V.²

23
- 0040155755
- Rajanbabu, T.V.; Nugent, W.A. J. Am. Chem. Soc., 1994, 116, 986.
- (1994) J. Am. Chem. Soc , vol.116 , pp. 986
- Rajanbabu, T.V.¹ Nugent, W.A.²

24
- 0038055611
- Gansauer, A.; Bluhm, H. Chem. Rev., 2000, 100, 2771.
- (2000) Chem. Rev , vol.100 , pp. 2771
- Gansauer, A.¹ Bluhm, H.²

25
- 0037009073
- Gansauer, A.; Pierobon, M.; B1uhm, H. Angew. Chem. Int. Ed. Engl., 2002, 41, 3206.
- Gansauer, A.; Pierobon, M.; B1uhm, H. Angew. Chem. Int. Ed. Engl., 2002, 41, 3206.

26
- 0344667717
- Gansauer, A.; Lauterbach, T.; Narayan, S. Angew. Chem. Int. Ed. Engl., 2003, 42, 5556.
- (2003) Angew. Chem. Int. Ed. Engl , vol.42 , pp. 5556
- Gansauer, A.¹ Lauterbach, T.² Narayan, S.³

27
- 7044237479
- Gansauer, A.; Lauterbach, T.; Geich-Gimbel, D. Chem. Eur. J., 2004, 10, 4983.
- (2004) Chem. Eur. J , vol.10 , pp. 4983
- Gansauer, A.¹ Lauterbach, T.² Geich-Gimbel, D.³

28
- 18744365768
- Friedrich, J.; DoIg, M.; Gansauer, A.; Geich-Gimbel, D.; Lauterbacht, T. J. Am. Chem. Soc., 2005, 127, 7071.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 7071
- Friedrich, J.¹ DoIg, M.² Gansauer, A.³ Geich-Gimbel, D.⁴ Lauterbacht, T.⁵

29
- 33746041112
- Daasbjerg, K.; Svith, H.; Grimme, S.; Gerenkamp, M.; Muck-Lichtenfeld, C.; Gansauer, A.; Barchuk, A.; Keller, F. Angew. Chem. Int. Ed. Engl., 2006, 45, 2041.
- (2006) Angew. Chem. Int. Ed. Engl , vol.45 , pp. 2041
- Daasbjerg, K.¹ Svith, H.² Grimme, S.³ Gerenkamp, M.⁴ Muck-Lichtenfeld, C.⁵ Gansauer, A.⁶ Barchuk, A.⁷ Keller, F.⁸

30
- 11144356778
- Justicia, J.; Rosales, A.; Bunuel, E.; Oller-Lopez, J.L.; Valdivia, N.; Haidour, A.; Oltra, J.E.; Barrero, A.F.; Cardenas, D.J.; Cuerva, J.M. Chem. Eur. J., 2004, 10, 1778.
- (2004) Chem. Eur. J , vol.10 , pp. 1778
- Justicia, J.¹ Rosales, A.² Bunuel, E.³ Oller-Lopez, J.L.⁴ Valdivia, N.⁵ Haidour, A.⁶ Oltra, J.E.⁷ Barrero, A.F.⁸ Cardenas, D.J.⁹ Cuerva, J.M.¹⁰

31
- 33748773349
- Gansauer, A.; Justicia, J.; Rosales, A.; Worgull, D.; Rinker, B.; Cuerva, J.M.; Oltra, J.E. Eur. J. Org. Chem., 2006, 4115.
- (2006) Eur. J. Org. Chem , pp. 4115
- Gansauer, A.¹ Justicia, J.² Rosales, A.³ Worgull, D.⁴ Rinker, B.⁵ Cuerva, J.M.⁶ Oltra, J.E.⁷

32
- 0041350396
- Barrero, A.F.; Rosales, A.; Cuerva, J.M.; Oltra, J.E. Org. Lett., 2003, 5, 1935.
- (2003) Org. Lett , vol.5 , pp. 1935
- Barrero, A.F.¹ Rosales, A.² Cuerva, J.M.³ Oltra, J.E.⁴

33
- 33645764493
- Gansauer, A.; Rosales, A.; Justicia, J. Synlett., 2006, 927.
- (2006) Synlett , pp. 927
- Gansauer, A.¹ Rosales, A.² Justicia, J.³

34
- 33746083184
- Gansauer, A.; Worgull, D.; Justicia, J. Synthesis, 2006, 2151.
- (2006) Synthesis , pp. 2151
- Gansauer, A.¹ Worgull, D.² Justicia, J.³

35
- 31444431583
- Snyder, S.A.; Corey, E.J. J. Am. Chem. Soc., 2006, 128, 740.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 740
- Snyder, S.A.¹ Corey, E.J.²

36
- 0004288915
- Hanessian, S, Ed, Dekker: New York
- Barton, D. H. R.; Ferreira, J. A.; Jaszberenyi, J. C. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Dekker: New York, 1997, 151.
- (1997) Preparative Carbohydrate Chemistry , pp. 151
- Barton, D.H.R.¹ Ferreira, J.A.² Jaszberenyi, J.C.³

37
- 0003123493
- Renaud, P, Mukund, P. S, Eds, Wiley-VCH: Weinheim
- Zard, S. Z. In Radicals in Organic Synthesis, Vol. 1; Renaud, P.; Mukund, P. S., Eds.; Wiley-VCH: Weinheim, 2001, 90.
- (2001) Radicals in Organic Synthesis , vol.1 , pp. 90
- Zard, S.Z.¹

38
- 4243854308
- Crich, D.; Quintero, L. Chem. Rev., 1989, 89, 1413.
- (1989) Chem. Rev , vol.89 , pp. 1413
- Crich, D.¹ Quintero, L.²

39
- 0034615857
- Akita, H.; Nozawa, M.; Mitsuda, A.; Ohsawa, H. Tetrahedron Asymmetry, 2000, 11, 1375.
- (2000) Tetrahedron Asymmetry , vol.11 , pp. 1375
- Akita, H.¹ Nozawa, M.² Mitsuda, A.³ Ohsawa, H.⁴

40
- 0033844397
- Ito, H.; Muranaka, T.; Mori, K.; Jin, Z.X.; Tokuda, H.; Nishino, H.; Yoshida, T. Chem. Pharm. Bull., 2000, 48, 1190.
- (2000) Chem. Pharm. Bull , vol.48 , pp. 1190
- Ito, H.¹ Muranaka, T.² Mori, K.³ Jin, Z.X.⁴ Tokuda, H.⁵ Nishino, H.⁶ Yoshida, T.⁷

41
- 38049162390
- Compound 11: Colourless oil. IR ν (cm-1) 3493, 2926, 2865, 1457, 1385, 1363, 1201, 1151, 1032, 888; 1H NMR (500 MHz, CDCl3) δ 3.66 (1H, dd, J= 11.6, 3.3 Hz, H-1la, 3.44 (1H, t, J= 11.6 Hz, H-11b, 3.24 (1H, dd, J= 3.8, 2.1 Hz, H-12a, 2.74 (1H, d, J= 3.8 Hz, H-12b, 2.01 (1H, ddt, J= 12.7, 4.7, 2.1 Hz, H-7eq, 1.91 (1H, dd, J= 10.1, 3.3 Hz, H-9, 1.87 (1H, dq, J= 13.5, 2.5 Hz, H-6a, 1.71 (1H, ddt, J= 12.8, 3.3, 1.5 Hz, H-leq, 1.63-1.49 (3H, m, H-6b, H2a, H2b, 1.46-1.42 (2H, m, H7ax, H3eq, 1.27-1.20 (2H, m, H-1ax, 12a, H-3ax, 1.10 (1H, dd, J= 12.5, 2.7 Hz, H-5, 0.93 (3H, s, H-15, 0.87 (3H, s, H-13, 0.86 (3H, s, H-14, 13C NMR (125 MHz, CDC13, DEPT) δ 61.82 (C, C-8, 58.95 (CH2, C-11, 54.69 (CH, C-5, 54.35 (CH, C-9, 51.86 (CH2, C-12, 41.79 (CH2, C-3, 39.18 (C, C-10, 38.88 (CH2, C-1, 36.28 C
- 2]: 238.1933, found: 238.1941.

42
- 38049115889
- Compound 12: Colourless oil. 1H NMR (300 MHz, CDCl3) δ 9.60 (1H, d, J= 4.0 Hz, H-11, 3.15 (1H, dd, J= 4.0, 2.0 Hz, H-12a, 2.74 (1H, dd, J= 4.0,1.2 Hz, H-12b, 2.50 (1H, d, J= 4.0 Hz, H-9, 2.03-1.82 (2H, m, H7a, H6a, 1.70-1.40 (6H, m, H1eq, H6b, H2a, H2b, H7ax, H3eq, 1.30-1.18 (2H, m, H1ax, H3ax, 1.22 (3H, s, Me-15),1.02 (1H, dd, J= 12.5, 2.8 Hz, H-5, 0.93 (3H, s, Me-15, 0.89 (3H, s, Me-13, 13C NMR (75 MHz, CDCl3, DEPT) δ 202.7 (CHO, C-11, 64.4 (CH, C-9, 57.8 (C, C-8, 54.0 (CH, C-5, 52.2 (CH2, C-12, 41.7 (CH2, C-3, 40.5 (C, C-10, 39.1 (CH2, C-1, 35.8 (CH2, C-7, 33.5 (CH3, C-15, 33.3 (C, C-4, 21.6 (CH3, C-14, 21.4 (CH2, C-6, 18.2 (CH2, C-2, 16.1 (CH3, C-13, HRMS El, m/z calcd for [C15H24O, 236.1776, found: 236.1782
- ]: 236.1776, found: 236.1782.

43
- 20544435021
- Barrero, A.F.; Herrador, M.M.; Quilez del Moral, J.F.; Arteaga, P.; Arteaga, J.F.; Piedra, M.; Sanchez, E.M. Org. Lett., 2005, 7, 2301.
- (2005) Org. Lett , vol.7 , pp. 2301
- Barrero, A.F.¹ Herrador, M.M.² Quilez del Moral, J.F.³ Arteaga, P.⁴ Arteaga, J.F.⁵ Piedra, M.⁶ Sanchez, E.M.⁷

44
- 0027371818
- Vidari, G.; Dapiaggi, A.; Zanoni, G.; Garlaschelli, L. Tetrahedron Lett., 1993, 34, 6485.
- (1993) Tetrahedron Lett , vol.34 , pp. 6485
- Vidari, G.¹ Dapiaggi, A.² Zanoni, G.³ Garlaschelli, L.⁴

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