Bibliografia
Bibliografia
1 Per recenti recensioni su tali sostanze, vedi: (a) M.C. Bibby, Drugs of the
Future 2002, 27,475-480; (b) A. Cirla, J. Mann, Nat. Prod. Rep. 2003, 20, 558-564; (c) R. Rossi, F. Bellina, A. Carpita, Sostanze organiche naturali e
loro derivati o analoghi strutturali con proprietà antineoplastiche, Ed. Plus,
2005, pp.27-38; (d) N. H. Nam, Curr. Med. Chem., 2003, 10, 1697-1722. 2 (a) G.R. Pettit, S.B. Singh, M.L. Niven, E. Hamel, J.M. Schmidt; J. Nat. Prod.
1987, 50, 119-131 (b) S.B. Singh, G.R. Pettit, J. Org. Chem.1989, 54, 4105-4114 (c) G. R. Pettit, S.B. Singh, M. L. Niven, J. Am. Chem.Soc., 1988, 110, 8539-8540
3 (a) G. R. Pettit, S.B. Singh, E. Hamel C.M. Lin, D.S. Alberts, D. Garcia-Kendall, Experientia 1989, 45, 209-211; Erratum in Experientia 1989, 45, 680; (b) A. Cirla, J. Mann, Nat. Prod. Rep. 2003, 20, 558-564.
4 (a) G. R. Pettit, S. B. Singh, M. R. Boyd, E. Hamel, R. K. Pettit, J. M. Schmidt, F. Hogan, J. Med Chem. 1995, 38, 1666-1672; (b) G. R. Pettit, G. M. Cragg, D. L. Herald, J. M. Schmidt, P. Lohavanijaya, Can. J. Chem., 1982, 60, 1374-1376; (c) E. Hamel, Med. Res. Rev. 1996, 16, 207-231; (d) G. R. Pettit, M. R. Rhodes, D. L. Herald, D. J. Chaplin, M. Stratford, R. K. Pettit, J. C. Capuis, D. Oliva, Anti-Cancer drug Des. 1989, 3, 249-254; (f) E. Hamel, in
Microtubule Proteins, J. Avila, Ed. Boca Raton, Fl, CRC Press, 1990, pp. 89-191.
5 (a) G. C. Dark, S. A. Hill, V. E. Prise, G.M. Tozer, G. R. Pettit, D. J. Chaplin,
Cancer Res. 1997, 57, 1829-1834; (b) D. J. Chaplin, G. R. Pettit, C. S. Parkins, S. A. Hill, Br. J. Cancer 1996, 74, S86-S88.
6 (a) A. T. Mc Grown, B. W. Fox, Cancer Chemother. Pharmacol. 1990, 26, 79-81; (b) A.A.E. El-Zayat, D.Degen, S.Drabek, G.M. Clark, G. R. Pettit, D.D. Van Hoff, Anticancer Drugs 1993, 4, 19-25; (c) S. M. Nabha, R. M. Mohammad, N.R. Wall, J. A Dutcher, G.R. Pettit, Proceedings of the 11th
NCI-EORTC-AACR Symposium, pubblicato come Supplemento al Clin. Cancer Res. 2000, Vol. 6 (Novembre).
7 (a)Vedi riferimento 4b; (b) G.R. Pettit, S.B. Singh, US Patent 4.966.237, 1991; (c) K. Gaukroger, J. A. Hadfield, L.A. Hepworth, N. J. Lawrence, A.T. McGrown, J. Org. Chem. 2001, 66, 8135-8138.
8 K. Oshumi, R. Nagawaka, Y. Fukuda, T. Hatanaka, Y. Morinaga, Y Nihei, K. Ohishi, Y. Suga, Y. Akiyama, T. Tsuji, J. Med. Chem. 1998, 41, 3022-3032. 9 (a)S. E. Holwell, P.A. Cooper, K. Grosios, J.W. Lippert III, G.R. Pettit, S.D.
Shnyder, M.C. Bibby, Anticancer Res. 2002, 22, 707-711.(b) G.R. Pettit, M.R. Rhodes, D.L. Herald, D.J. Chaplin, M.R.L. Stratford, E. Hamel, R.K. Pettit, J.C. Capuis, D. Oliva, Anti-Cancer Drug Des. 1998, 13, 981-993; (c) G. R. Pettit, M. R. Rhodes, Anti-Cancer Drug Des. 1998, 13, 183-191; (d) S.E. Holwell, P.A. Cooper, M.J. Thompson, G.R. Pettit, L.W. Lippert III, S. W. Martin, M. C. Bibby, Anti-Cancer Res. 2002, 22 (6C), 3933-3940; (e) C. Kanthou, O. Greco, A. Stratford, I. Cook, R. Knight, O. Benzakour, G. Tozer,
Am. J. Pathol. 2004, 165, 1401-1411.
10 A. Dowlati, K. Robertson, M. Cooney, W.P. Petros, M. Stratford, J. Jesberger, N. Rafie, B. Overmoyer, V. Makkar, B. Stambler, A. Taylor, J. Waas, J.S. Lewin, K.R. McCrae, S.C. Remick, Cancer Res. 2002, 62, 3408-3416.
11 (a) R.T. Brown, B. W. Fox, J. A. Hadfield, A. T. McGown, S.P. Mayalarp, G.R: Pettit, J.A. Woods, J. Chem. Soc., Perkin Trans. I, 1995, 577-581. (b) F. Orsini, F. Pellizzoni, B. Bellini, G. Miglierini, Carbohydr. Res. 1997, 301, 95-109. (c) K. Oshumi, T. Hatanaka, R. Nakagawa, Y. Fukuda, Y. Morinaga, Y. Suga, Y. Nihei, K. Ohishi, Y. Akiyama, T. Tsuji, Anti-Cancer Drug Des. 1999, 14, 539-548. (d) S. B. Bedford, C.P. Quarterman, D. L. Rathbone, J.A. Slack, R. J. Griffin, M. F. G. Stevens, Bioorg. Med. Chem. Lett. 1996, 6, 157-160.
12 P.D. Davis, G.J. Daugherty, D.C. Blakey, S.M. Galbraith, G.M. Tozer, A.H. Holder, M.A. Naylor, J. Nolan, M.R.L. Stratford, D.J. Chaplin, S.A. Hill,
Cancer Res., 2002, 62, 7247-7253.
13 G. Micheletti, M. Poli, P. Borsotti, M. Martinelli, B. Imberbi, G. Taraboletti, R. Giavazzi, Cancer Res. 2003, 63, 1534-1537, e bibliografia ivi citata.
14 K. Ohsuni, R. Nakagawa, Y. Fukuda, T. Hatanaka, Y. Morinaga, Y. Nihei, Y. Ohishi, Y. Suga, Y. Akiyama, T. Tsuji, J. Med. Chem., 1998, 41, 3022-3032. 15 G.R. Pettit, M. R. Rhodes, D. L. Herald, E. Hamel,J. M. Schmidt, R. K. Pettit
J. Med. Chem. 2005, 48 (12), 4087-4099.
16 H. E. Zimmerman, D. W. Wilson, J. Org. Chem. 1995, 60, 692.
17 (a) K. Oshumi, R. Nakagawa, Y. Fukuda, T. Hatanaka, Y. Morinaga, Y. Nihei, K. Ohishi, Y. Suga, Y. Akiyama, T. Tsuji, J. Med. Chem. 1998, 41, 3022. (b) K. Oshumi, T. Hatanaka, R. Nakagawa, Y. Fukuda, Y. Morinaga, Y. Suga, Y. Nihei, K. Ohishi, Y. Akiyama, T. Tsuji, Anti-Cancer Drug Des. 1999, 14, 539.
18 C. Borrel, S. Thoret, X. Cachet, D. Gènard, F. Tillequin, M. Koch, S. Michel
Bioorg. Med. Chem. 2005, 13, 3853-3864.
19 G. Giannini, M. Marzi, D. Alloatti, M. O. Tinti, T. Riccioni, M. Marcellini,
Brit. UK Pat. Appl. 2005, 34 pp, GB 2403949.
20 M. Banerjee, A. Poddar, G. Mitra, A. Surolia, T. Owa, B. Bhattacharyya, J.
Med. Chem. 2005, 48, 547-555.
21 S. L. Gwaltney II, H.M. Imade, K.J. Barr, Q. Li, L. Gehrke, R. B. Credo, R. B. Warner, J. Y. Lee, P. Kovar, J. wang, M. A. Nukkala, N. A. Zielinski, D. Frost, S.C. Ng, H. L. Sham, Bioorg. Med. Chem. Lett. 2001, 11, 871-874. 22 N.J. Lawrence, D. Renninson, M. Woo, A.T. McGown, J.A. Hadfield Bioorg.
Med. Chem. Lett. 2001, 11, 51-54.
23 (a) G.R. Pettit, B. Toki, D.L. Herald, P. Verdier-Pinard, M. R. Boyd, E. Hamel, R.K. Pettit, J. Med. Chem. 1998, 41, 1688-1695. (b) G.R. Pettit, M.P. Grealish, D.L. Herald, M.R. Boyd, E. Hamel, R.K: Petti, J. Med. Chem. 2000,
43, 2731-2737. (c) G.R. Pettit, J.W. Lippert, D.L. Herald, J. Org. Chem. 2000,
65, 7438-7444. (d) J.P. Liou, C.W. Chang, J.S. Song, Y. N. Yang, C. F. Yeh,
H. Y. Tseng, Y.K. Lo, Y.L. Chang, C.M. Chang, H.P. Hseih, J. Med. Chem. 2002, 45, 2556-2562 (e) J.P: Liou, J. Y. Chang, C.W. Chang, N. Mahindron, F. M. Kuo, H.P. Hsieh, J. Chem. Med. 2004, 47, 2897-2905.
24 K. Oshuni, T. Hatanaka, K. Fujita, R. Nagakawa, Y. Fukuda, Y Nihey, Y. Suga, Y. Morinaga, Y. akiyama, T. Tsuji, Bioorg. Med. Chem. Lett. 1998, 8, 3153-3158.
25 L. Wang, K.W. Woods, Q. Li, K.J. Barr, R.W. McCroskey, S.M. Hannick, L. Gherke, R.B. Credo, Y.H. Hui, K. Marsh, R. Warner, J.Y. Lee, N. Zielinski-Mozng, D. Frost, S.H. Rosenberg, H.L. Sham, J. Med. Chem. 2002, 45, 1697-1711.
26 A. B. S. Maya, C. Perez-Melero, N. Salvador, R. Pelaez, E. Caballero, M. Medarde, Bioorg. Med. Chem. 2005, 13, 2097-2107.
27 G. C. Tron, F Pagliai E. Del Grosso, A. A. Genazzani, G. Sorba, J. Med.
Chem. 2005, 48, 3260-3268.
28 D. Simoni, G. Grisolia, G. Giannini, M. Roberti, R. Rondanin, L. Piccagli, R. Baruchello, M. Rossi, R. Romagnoli, F. P. Invidiata, S. Grimaudo, M. K. Jung, E. Hamel, N. Gebbia, L. Crotsa,V. Abbadessa, A. Di Cristina, L. Dusonchet, M. Meli, M. Tolomeo, J. Med. Chem. 2005, 48, 723-736.
29 N. H. Nam, Y. Kim, Y.J. You, D.H. Hong, H.M. Kim, B.Z. Ahn, Bioorg.
Med. Chem. Lett. 2001, 11, 3073-3076.
30 L. Sun, N.I. Vasilevich, J.A. Fuselier, S.J. Hocart, D.H. Coy, Bioorg. Med.
Chem. Lett. 2004, 14, 2041-2046.
31 (a) B.L. Flynn, G.P. Flynn, E. Hamel, M.K. Jung, Bioorg. Med. Chem. Lett. 2001, 11, 2341-2343 (b) Z. Chen, V. P. Mocharla, J. M. Farmer, G.R. Pettit, E. Hamel, K.G. Pinney, J. Org. Chem. 2000, 65, 8811-8815.
32 (a) R. Shirai, T. Okabe, S. Iwasaki, Heterocycles, 1997, 46, 145-148. (b) R. Shirai, H. Takayama, A. Nishikawa, Y. Koiso, Y. Hashimoto, Bioorg. Med.
Chem. Lett. 1998, 8, 1997-2000 (c) Y. Kim, N.H. Nam, Y.J. You, B.Z. Ahn,
Bioorg. Med. Chem. Lett. 2002, 12, 719-722.
33 N.H. Nam, Y. Kim, Y.J. You, D.H. Hong, H.M. Kim, B.Z. Ahn, Bioorg. Med.
Chem. Lett. 2002,12, 1955-1958.
34 F. Bellina, C. Anselmi, F. Martina, R. Rossi, Eur. J. Org. Chem. 2003, 2290-2302
35 F. Bellina, E. Falchi, R. Rossi, XVII Convegno Nazionale della Divisione di
Chimica Farmaceutica, Pisa, 6-10 Settembre 2004, Atti del Convegno, P8.
36 3,4-Diaril-2(5H)-furanoni citotossici sono stati sintetizzati per la prima volta da Y. Kim, N.H. Nam, Y.J. You, B.Z.A. Ahn, Bioorg. Med. Chem. Lett. 2002,
12, 719-722.
37 F. Bellina, E. Falchi, R. Rossi, Tetrahedron, 2003, 59, 9091-9100.
38 G. De Martino, G. La Regina, A. Coluccia, M. C. Edler, M.C. Barbera, A. Brancale, E. Wilcox, E. Hamel, M. Artico, R. Silvestri J. Med. Chem. 2004,
47, 6120-6123.
39 C. Bailly, C. Bal, P. Barbier, S. Combes, J.P. Finet, H.P. Hildebrand, V. Peyrot, N. Wattez, J. Med. Chem. 2003, 46, 5437-5444.
40 (a) A. Jordan, J.A. Hadfield, N.J. Lawrence, A.T. McGrown, Med. Res. Rev. 1998, 259-296. (b) M. Cushmann, D. Nagarathnam, D. Gopal, H.M. He, C.M. Lin, E. Hamel, J. Med. Chem. 1992, 35, 2293-2306. (c) Z. Getahun, L. Jurd, P.S. Chu, C.M. Lin, E. Hamel, J. Med. Chem. 1992, 35, 1058-1067. (d) Q. Shi, K. Chen, S.L. Morris-Natschke, K. H. Lee, Curr. Pharm. Des. 1998, 4, 219-248
41 (a) A.B.S. Maya, B. Le Rey, R.P. Lamamie de Clairac, E. Caballero, I. Barasoain, J.M. Andreu, M. Medarde Bioorg. Med. Chem. Lett. 2000, 10, 2549-2551. (b) A.B.S. Maya, C. Perez-Melero, C. Mateo, D. Alonso, J. L. Fernandez, C. Gajate, F. Mollinedo, R. Pelaez, E. Caballero, M. Medarde, J.
Med. Chem. 2005, 48, 556-568. (c) A.B.S. Maya, C. Perez-Melero, N. Salvador, R. Pelaez, E. Caballero, M. Medarde Bioorg. Med. Chem. 2005, 13, 2097-2107.
42 A.B.S. Maya, B. Le Rey, R.P. Lamamie de Clairac, E. Caballero, I. Barasoain, J.M. Andreu, M. Medarde Bioorg. Med. Chem. Lett. 2000, 10, 2549-2551.
43 J.P. Liou,Y.L. Chang, F.M. Kuo, C.W. Chang, H.Y. Tseng, C.C. Wang, Y.N. Yang, J.Y. Chang, S.J. Lee, H.P. Hsieh, J. Med. Chem. 2004, 47, 4247-4257. 44 M. Banerjee, A. Poddar, G. Mitra, A. Surolia, T. Owa, B. Bhattacharyya, J.
Med. Chem. 2005, 48, 547-555.
45 K. Oshuni, R. Nakagawa, Y. Fukuda, T. Hatanaka, Y. Morinaga, Y. Nihei, Y. Ohishi, Y. Suga, Y. Akiyama, T. Tsuji, J. Med. Chem. 1998, 41, 3022-3032. 46 N. J. Lawrence, L.A. Hepworth, D. Rennison, A.T. McGown, J.A. Hadfield, J.
Fluorine Chem. 2003, 123, 101-108.
47 G.R. Pettit, M. R. Rhodes, D. L. Herald, E. Hamel,J. M. Schmidt, R. K. Pettit
J. Med. Chem. 2005, 48 (12), 4087-4099.
48 C. Borrel, S. Thoret, X. Cachet, D. Gènard, F. Tillequin, M. Koch, S. Michel
Bioorg. Med. Chem. 2005, 13, 3853-3864.
49 A.B.S. Maya, B. Le Rey, R.P. Lamamie de Clairac, E. Caballero, I. Barasoain, J.M. Andreu, M. Medarde Bioorg. Med. Chem. Lett. 2000, 10, 2549-2551. 50 C. Perez-Melero, A.B.S. Maya, B. del Rey, R. Pelaez, E. Caballero, M.
Medarde, Bioorg. Med. Chem. Lett. 2004, 14, 3771-3774
51 A.B.S. Maya, C. Perez-Melero, C. Mateo, D. Alonso, J.L. Fernandez, C. Gajate, F. Mollinedo, R. Pelaez, E. Caballero, M. Medarde, J. Med. Chem. 2005, 48, 556-568.
52 M. Medarde, A. Ramos, E. Caballero, R. Pelaz-Lamamiè de Clairac, J.L. Lopez, D. Garcia Gravalos, A. San Felicia, Eur. J. Med. Chem. 1998, 33, 71-77.
53 (a) F. Bellina, E. Falchi, R.Rossi, Tetrahedron 2003, 59, 9091-9100. (b) F. Bellina, E. Falchi, R. Rossi, XXI Congresso Nazionale della Società Chimica
Italiana SCI 2003, Torino-Italy, 22-27 Giugno 2003, Atti, vol. 1, OR-CO-010.
54 Per quanto riguarda la biologia cellulare del citoscheletro vedere Molecular
Biology of the Cell, 4th ed. Alberts, Bruce; Johnson, Alexander; Lewis, Julian; Raff, Martin; Roberts,
Keith; Walter, Peter
New York: Garland Publishing; 2002, Parte IV, Cap. 16.
55 Per quanto riguarda l’angiogenesi e l’apoptosi vedere Cancer Medicine, 6th ed. Kufe, Donald W.; Pollock, Raphael E.; Weichselbaum, Ralph R.; Bast, Robert C., Jr.; Gansler, Ted S.; Holland, James F.; Frei III, Emil, editors. Hamilton (Canada): BC Deker Inc.; 2003, Parte II, Sez. I, Cap. 4 e 11.
56 (a) E. Charbaut, P.A. Curmi, S. Ozon, S. Lachkar, V. Redekert, A. Sobel, J.
biol. Chem. 2001, 276, 16146-16154. (b)R.B.G. Ravelli, B. Gigant, P.A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, M. Knossow, Nature, 2004, 428, 198-202.
57 A. Duflos, A. Kruczynski, J.M. Barrer, Curr. Med. Chem. Anti-Cancer
Agents, 2002, 2, 55-70.
58 (a) G.M. Cragg, D.J. Newmann, J. Nat. Prod., 2004, 67, 232-244 e riferimenti ivi citati; (b) C.M. Haskell, in Cancer Treatment, C.M. Haskell Ed., 4th ed. Philadelphia, W.B. Saunders Co., 1995, pp. 78-165.
59 Per recensioni sulla chimica e la biologia del tassolo vedi: (a) K.C: Nicolaou, W.M. Dai, R.K. Guy, Angew. Chem. Int. Ed. Engl. 1994, 33, 15-44; (b) D.G.I . Kingston, Chem. Commun., 2001, 867-880, e bibliografia ivi citata (c) V. Farina, Ed., The Chemistry and Pharmacology of Taxol and its Derivatives, New York, Elsevier, 1995; (d) G.I. Georg, T.C. Boge, Z.S. Cheruvallath, J.S. Clowers, G.C.B. Harriman, M. Hepperle, H. Park, in The Medicinal Chemistry
Suffness, Ed., Taxol: science and Applications, CRC Press Inc., Boca Raton,
Fla., 1995.
60 (a)W. Fan, Biochem. Pharmacol. 1999, 57, 1215-1221; (b) T.H. Wang, H.S. Wang, Y.K. Soong, Cancer, 2000, 88, 2619-2628; (c) D.J. Rodi, R.W. Janes, H.J. Sanganee, R.A. Holton, B.A. Wallace, L. Makowski, J. Mol. Biol. 1999,
285, 197-203. (d) C.D. Scatena, Z.A. Stewart, D. Mays, L.J. Tang, C.J.
Keefer, S.D. Leach, J.A. Pietenpol, J. Biol. Chem. 1998, 273, 30777-30784; (e) M.V. Blagoskolonny, P. Giannakakou, W.S. el-Deiry, D.G. Kingston, P.I. Higgs, L. Neckers, T. Fojo, Cancer Res. 1997, 57, 130-135.
61 (a) O. Boyè, A. Brossi, in The Alkaloids, A. Brossi, G.A. Cordell, Eds. New York, Academic Press, 1992, vol. 41, pp. 125-176, e riferimenti ivi citati; (b) A. Brossi, H.H. Lee, H.J.C. Yeh, Helv. Chem. Acta, 1999, 82, 1223-1224; (c) M.V. King, J.L. De Vries, R. Pepinsky, Acta Crystallogr. Sect. B. 1952, 155, 50.
62 D. Panda, J.E. Daijo, M.A. Jordan, L. Wilson, Biochemistry, 1995, 34, 9921-9929.
63 H. Corrodi, E. Hardegger, Helv. Chim. Acta, 1955, 38, 2030-2033. 64 A. Brossi, Med. Res. Rev., 1994, 14, 665-691.
65 I. Ringel, H. Sternlicht, Biochemistry, 1984, 23, 5644-5653.
66 (a) B. Battacharyya, J. Wolff, Proc. Natl. Acad. Sci. U.S.A., 1974, 71, 2627-2631; (b) B. Battacharyya, J. Wolff, Arch. Biochem. Biophys., 1975, 167, 264-269.
67 R. B. G. Ravelli, B. Gigant, P. A. Curmi, I. Jourdain, S. Lachkar, A. Sobel, M. Knossow, Nature, 2004, 428, 198-202.
68 S. Ducki, G. Mackenzie, N.J. Lawrence, J.P. Snyder, J. Med. Chem., 2005, 48, 457-465.
69 (a) A. Jordan, J.A. Hadfield, N.J. Lawrence, A.T. McGown, Med. Res. Rev., 1998, 259-296. (b) Z. Getahun, L. Jurd, P.S. Chu, C.M. Lin, E. Hamel, J. Med.
Chem., 1992, 35, 1058-1067; (c) Q.Shi, K. Chen, S.L. Morris- Natschke, K.H. Lee, Curr. Pharm. Des., 1998, 4, 219-248.
70 H.M. Nam, Curr. Med. Chem., 2003, 10, 1697-1722.
71 A.B.S. Maya, C. Perez-Melero, C. Mateo, D. Alonso, J. L. Fernandez, C. Gasate, F. Mollinedo, R. Pelaez, E. Caballero, M. Medarde, J. Med. Chem., 2005, 48, 556-568.
72 P. E. Thorpe, Clin. Cancer Res., 2004, 10, 415-427.
73 S. M. Nabha, R.M. Mohammad, M. H. Dandashi, B. Coupaye-Gerard, A. Aboukameel, G.R. Pettit, A.M. al-Katib, Clin. Cancer Res. 2002, 8, 2735-2741
74 M. O. Hengartner, Nature, 2000, 407, 770-776.
75 (a) F. Bellina, S. Cauteruccio, L. Mannina, R. Rossi, S. Viel, J. Org. Chem., 2005, 70, 3997-4005; (b) F. Bellina, A. Carpita, L. Mannocci, R. Rossi, Eur.
J. Org. Chem., 2004, 2610-2619; (c) F. Bellina, C. Anselmi, F. Martina, R. Rossi, Eur. J. Org. Chem., 2003, 2290-2302; (d) F. Bellina, E. Falchi, R. Rossi Tetrahedron, 2003, 59, 9091-9100; (e) R. Rossi, A. Carpita, F. Bellina, P. Stabile, L. Mannina, Tetrahedron, 2003, 59, 2067-208; (f) F. Bellina, C. Anselmi, S. Viel, L. Mannina, R. Rossi, Tetrahedron, 2001, 57, 9997-10007; (g) A. Carpita, S. Barconi, R. Rossi, Tetr, Asymmetry, 2005, 16, 2501-2508. 76 Per alcuni esempi di 2H-piran-2-oni naturali con attività antitumorale, vedere:
(a) T. Nogawa, Y. Kamano, G. R. Pettit, J. Nat. Prod. 2001, 64, 1148; (b) S. Numazawa, Y. Monma, T. Yamamoto, T. Yoshida, Y. Kuroiwa, Leucemia
Res. 1995, 19, 945; (c) Y. Jing, H. Ohizumi, N. Kawazua, S. Hashimoto, Y. Masuda, S. Nakaio, t. Yoshida, Y. Kuroiwa, K. Nakaya, Jpn. J. Cancer Res. 1994, 54, 645; (d) J.L. McCarmick, T.C. McKee, M.J. Cardellina II, M. Leid, M.R. Boid, J. Nat. Prod., 1996, 59, 1047; (e) Y Kamano, T. Nagawa, A. Yamoshita, M. Mayashi, M.Inone, P. Drašor, G.R. Pettit, J. Nat. Prod., 2002,
65, 1001.
77 Per esempi di isocumarine naturali con attività antitumorale, vedere: (a)A.C. White, J.B. Gloer, J.A. Scott, D. Mallok, J. Nat. Prod. 1996, 59, 765-769; (b) J.M. Lee, Y.J. Park, H.S. Kim, Y.S. Hong, K.W. Kim, J.J. Lee, Antibiotic, 2001, 54, 463-466; (c) K. Umehara, M. Matsumoto, M. Nabamura, T. Miyase, K. Kuronyanagi, M. Noguhi, Chem. Pharm. Bull., 2000, 48, 566-567.
78 Per alcuni esempi di 2H-piran-2-oni non naturali con proprietà antitumorali, vedere: (a) I. J. S. Fairlamb, L.R. Morrison, J.M. dickinson, F.Y. Lu, J.P. Shmidt, Bioorg. Med. Chem., 2004, 12, 4285-4299; (b) B. Proksa, D. Uhrin, T. Fusha, Pharmazia, 1986, 41, 703-704; (c) M. Ye, G. Qu, G. Hongzhu, D. Guo, J. Ster. Biochem. Mol. Biol., 2004, 91, 87-98; (d) L.R. Morrison, J.M. Dickinson, I.J.S. Fairlamb, Bioorg. Med. Chem. Lett., 2003, 13, 2667-2671; (e) F. Borges, F. Roleira, N. Milhazes, L. Santana, E. Uriartre, Curr. Med.
Chem., 2005, 12, 887-916.
79 A. Gehrt, G. Erkel, T. Anke, O. Sterner, Z. Naturforsch. 1998, 53c, 89-92. 80 F. Bellina, A. Carpita, L. Mannocci, R. Rossi, Eur. J. Org. Chem., 2004,
2610-2619.
81 Y. Horiguchi, T. Saitoh, N. Koseki, H. Suzuki, J. Toda, T. Sano,
Heterocycles, 2000, 53 (6) 1329-1336.
82 T. Dubuffet, B. Cimitiere, G. La Vielle, Synth. Comm., 1997, 27(7), 1123-1131
83 Per una serie di recenti metodi di sintesi di aldeidi 25, vedere: a) A. Procopio, R. Delpozzo, A. De Nino, M. Nardi, G. Sindona, A. Tagarelli, Synlett, 2004,
14, 2633-2635; b) R. Olivera, R. SanMartin, I. Tellitu, E. Dominguez, Tetrahedron, 2002, 58(15), 3021-3037; c) K.A. Bhatia, K. J. Eash, N. M. Leonard, M.C. Oswald, R. S. Mohan, Tetr. Lett., 2001, 42(46), 8129-8132; d) S. Sankararaman, J. E. Nesakumar, J. Chem. Soc., Perkin Trans. I: Org.
Bioorg. Chem., 1999, 21, 3173-3175; e) J. J. Eisch, S. K. Suresh, M. Behrooz,
J. Org. Chem., 1985, 50(19), 3674-3676; f) K. Miyauchi, K. Hori, T. Hirai, M. Takebayashi, T. Ibatu, Bull. Chem. Soc. Japn., 1985, 54, 2142-2146.
84 a) F. Bellina, M. Biagetti, A. Carpita, R. Rossi, Tetrahedron, 2001, 57, 2857-2870; b) F. Bellina, M. Biagetti, A. Carpita, R. Rossi, Tetr. Lett., 2001, 42, 2859-2863; c) F. Bellina, M. Biagetti, A. Carpita, R. Rossi, 3rd Italian-German Symposium on Organic Chemistry, Ravenna, 30 Marzo-1Aprile 2001, Atti P02. d) F. Bellina, M. Biagetti, A. Carpita, S. Viel, L. Mannina, R. Rossi, Eur.
J. Org. Chem., 2002, 1063-1076; e) M. Biagetti, F. Bellina, A. Carpita, P. Stabile, R. Rossi, Tetrahedron, 2002, 58, 5023-5028; f) F. Bellina, M. Biagetti, A. Carpita, R. Rossi, 23rd Int. Symposium on the Chemistry of
Natural Product, Firenze, 28 Luglio-2 Agosto 2002, P23; g) M. Biagetti, F. Bellina, A. Carpita, R. Rossi, Tetr. Lett., 2003, 44(3), 607-610; h) R. Rossi, A. Carpita, F. Bellina, P. Stabile, L. Mannina, Tetrahedron, 2003, 59, 2067-2081; i) ref. 80.
85 a) A. Belonger, P. Brassard, Can. J. Chem., 1975, 53, 201-208; b) A.A.M. Houwen-Claassen, A.J.H. Klunder, B. Zwanenburg, Tetrahedron, 1989,
E.L. Clennan, J. Org. Chem., 1984, 49, 4523-4531; d) J.W. Pavlik, A.P. Spada, T.E. Snead, J. Org. Chem., 1985, 50, 3046-3050; e) A.K. Mandal, D.G. Jawalkar, J. Org. Chem. 1989, 54, 2364-2369; f) N.P. Shusherina, E.A. Luk'yanets, R.Y. Levina, Zhurn. Obsh. Khim., 1964, 34(1), 20-24; g) G. Märkl, R. Fuchs, Tetr. Lett., 1972, 46, 4691-4694; h) L. Crombie, M. Eskins, D.E. Games, C. Loader, J. Chem. Soc. Perkin Trans. I, 1977, 478-482; i) G. Dionne, Ch. R. Engel, Can. J. Chem., 1978, 56, 419-423; l) A. Valla, F. Zentz, D. Cartier, R. Labia, Nat. Prod. Lett., 2000, 14(6), 417-423; m) R.C. Larock, M.J. Doty, X. Han, J. Org. Chem., 1999, 64(24), 8770-8779; n) M. Kotora, M. Ishikawa, F.Y. Tsai, T. Takahashi, Tetrahedron, 1999, 55, 4969-4578; o) R. Rossi, F. Bellina, M. Biagetti, A. Catanese, L. Mannina, Tetr. Lett., 2000, 41, 5281-5286.
86 a) T. Yao, R.C. Larock, Tetr. Lett., 2002, 43, 7401-7404; b) T. Yao, R.C. Larock, J. Org. Chem., 2003, 68, 5936-5942.
87 a) G. A. Krafft, J. A. Katzenellenbogen, J. Am. Chem. Soc., 1981, 103, 5459-5466; b) S. B. Daniels, E. Cooney, M. J. Sofia, P. K. Chakravarty, J. A. Katzenellenbogen, J. Biol. Chem., 1983, 258, 15046-15053; c) R. W. Spencer, T. F. Tam, E. Thomas, V.J. Robinson, A. Krantz, J. Am. Chem. Soc., 1986,
108, 5589-5597; d) A. Nagarajan, T. R. Balasubramanian, Indian J. Chem. Sect. B, 1988, 27, 380; e) J. T. Doi, G.W. Luehr, D. Del Carmen, B.C. Lippsmeyer, J. Org. Chem., 1989, 54, 2764-2767; f) N. G. Kundu, M. Pal, B. Nandi, J. Chem. Soc., Perkin Trans. 1, 1998, 561-568.
88 Per alcuni riferimenti su questo soggetto, vedere: a) M. D. Dowle, D. I. Davies, Chem. Soc. Rev., 1979, 171-197; b) G. Cardillo, M. Orena,
Tetrahedron, 1990, 46, 3321-3408; c) K. E. Harding, T. H. Tiner,
Comprehensive Organic Synthesis, B. M. Trost, I. Fleming, Eds; Pergamon:
Oxford, 1991; vol. 4, pp. 363-421; d) R. T. Brown, D. M. Duckworth, C. A. M. Santos, Tetr. Lett., 1991, 32, 1987-1990; e) S.B. Bedford, G. Fenton, D. W. Knight, D. E. Shaw, J. Chem. Soc., Perkin Trans. 1, 1996, 1505-1509; f) M. C. Roux, R. Paugam, G. Rousseau, J. Org. Chem., 2001, 66, 4304-4310 ; g) S. P. Chavan, A. K. Sharma, Tetr. Lett., 2001, 42, 4923-4924 e riferimenti ivi citati; h) S. Rousset, J. Thibonnet, M. Abarbri, A. Duchêne, J. L. Parrain,
Synlett, 2000, 260-262; i) G. Delle Monache, D. Misiti, P. Salvatore, G. Zappia, Tetr.: Asymmetry, 2000, 11, 1137-1149.
89 a) V. Jäger, H. J. Günther, Tetr. Lett. 1977, 29, 2543-2546; b) D.G. Garratt, M. D. Ryan, P. L. Beaulieu, J. Org. Chem. 1980, 45, 839-845; c) J. A. Macritchie, T. M. Peakman, A. Silcock, C. L. Willis, Tetr. Lett., 1998, 39, 7415-7418.
90 Per informazioni sul cross-coupling di Sonogashira, vedere: R. Rossi, A. Carpita, F. Bellina, Org. Prep. Proc., 1995, 27(2), 127-160 e bibliografia ivi citata.
91 Per alcuni esempi di sintesi di (Z)-2-penten-4-inoati 5 sostituiti, vedere: a)S. Ma, X. Lu, J. Chem. Soc. Chem. Commun., 1990, 1643; b) S. Ma, X. Lu, Tetr.
Lett., 1990, 31, 7653; c) S. Ma, X. Lu, Z. Li, J. Org. Chem., 1992, 15, 709; d) X. Lu, X. Huang, S. Ma, Tetr. Lett. 1992, 33(18), 2535-2538.
92 a) R. Eastmond, D.R.M. Walton, Tetrahedron, 1972, 28, 4591-4599; b)R. Eastmond, T. R. Johnson, D. R. M. Walton, Tetrahedron, 1972, 28, 4601-4616; c) E. Negishi, N. Okukado, S. F. Lovich, F. T. Luo, J. Org. Chem., 1984, 49, 2629-2632; d) A. S. Kende, C. A. Smith, J. Org. Chem., 1988, 53, 2655-2657; e) L.H. Lee, V. Lynch, R. J. Lagow, J. Chem. Soc., Perkin Trans.
1, 2000, 2805-2809; f) R. Rossi, F. Bellina, A. Catanese, L. Mannina, D. Valensin, Tetrahedron, 2000, 56, 479-487; g) M. Qian, E. Negishi, Org. Proc.
Res. Dev., 2003, 7, 412-417; h) M. S. Karatholuvhu, P. L. Fuchs, J. A. chem.
Soc. 2004, 128, 14314-14315.
93 Per informazioni sul cross-coupling di Cadiot-Chodkiewicz, vedere: a) P. Cadiot, W. Chodkiewicz, In Chemistry of Acetylenes, H. G. Viehe, Ed.; Marcel Dekker: New York, 1969, pp. 597-647; b) W. Chodkiewicz, Ann.
Chim. (Paris) 1975, 2, 819-869; c) G. Eglinton, W. McCrae, Adv. Org. Chem., 1963, 4, 225-328; d) P. Siemens, R.C. Livingston, F. Diederich, Angew.
Chem. Int. Ed. Engl., 2000, 39, 2632-2657.
94 I. Nishikawa, S. Shikuya, S. Hosokawa, M. Isobe, Synlett, 1994, 485-486. 95 D. Grandjean, P. Pale, J. Churche, Tetrahedron, 1993, 49(24), 5225-5236. 96 F. Bellina, A. Carpita, R. Rossi, Synthesis, 2004, 15, 2419-2440 e bibliografia
ivi citata.
97 a) F. Bellina, A. Carpita, D. Ciucci, M. De Santis, R. Rossi, Tetrahedron, 1993, 49, 4677; b) R. Rossi, F. Bellina, E. Raugei, Synlett, 2000, 1749; c) V. Farina, S. Kapadia, B. Krishnan, C. Wang, L. S. Liebeskind, J. Org. Chem., 1994, 59, 5905; d) R. Rossi, F. Bellina, M. Biagetti,, Synth. Comm., 1999, 29, 3415; e) H.M.R. Hoffmann, K. Gerlach, E. Lattmann, Synthesis, 1996, 164. 98 Per alcune reazioni di bromodesililazione su vinilsilani, vedere: a) R.B. Miller,
G. Mc Garvey, J. Rg. Chem., 1978, 43, 4424; b) R.B: Miller, G. Mc Garvey,
Synth. Commun. 1977, 7, 475.
99 V. P. Bui, T. Hudlicky, T.V. Hansen, Y. Stenstrom, Tetr. Lett., 2002, 43(15), 2839-2841.
100 A. Carpita, R. Rossi, C.A. Veracini, Tetrahedron, 1985, 41(10), 1919-1929. 101 K.S. Feldmann, J. Org. Chem., 1997, 62(15), 4983-4990.
102 Per alcuni esempi di questi metodi vedere: a) M. Seto, Y. Aramaki, T. Okawa, N. Miyamoto, K. Aikawa, N. Kanzaki, S. Niwa, Y. Iizawa, M. Baba, M. Shiraishi, Chem. Pharm. Bull., 2004, 52(5), 577-590, b) M. A. Zhuravel S. T. Nguyen, Tetr. Lett., 2001, 42, 7925-7928.
103 H. Fang, G. Kaur, J. Yan, B. Wang, Tetr. Lett., 2005, 46, 1671-1674.
104 Nel nostro laboratorio è stata usata anche con acidi (Z)-3-bromopropenoici: vedere riferimento 84a
105 Vedi riferimento 80 e bibliografia ivi citata.
106 a) F. Bellina et. Al. Tetrahedron, 2000, 56, 479-487; b)V. Ratovelomana, G. Linstrumelle, Tetr. Lett., 1981, 22, 315-318; c) R. Eastmond, D.R.M: Walton,
Tetrahedron, 1992, 28, 4591-4599.
107 Sull’instabilità di tali diini vedere: a) A.S. Kende, C.A. Smith, J. Org. Chem., 1988, 53, 2655-2657; b) R. Eastmond, T.R. Johnson, D.R. M. Walton,
Tetrahedron, 1972, 28, 4601-4616; c) R. Eastmond, D.R.M. Walton,
Tetrahedron, 1972, 28, 4591-4599; d) E. Negishi, N. Okukodo, S.f. larich, F.T. Luo, J. Org. Chem., 1984, 49, 2629-2632.
108 J. Kristensen, M. Lysèn, P. Vedasø, M. Begtrup, Org. Lett., 2001, 3(10), 1435-1437.
109 S. Urgaonkar, J.G. Verkade, J. Org. Chem. 2004, 69, 5752-5755. 110 D.R. Coulson, Inorg. Synth. 1972, 13, 121
111 T. Hayashi, M. Konishi, Y. Kobori, M. Kumada, T. Higuchi, K. Hirotsu, J:
Am. Chem. Soc., 1984, 106, 158.
112 M. X.-W Jiang, M Rawat, W. D Wulff, J. Am. Chem. Soc., 2004, 126(19), 5970-5971.
113 M. Abarbi, J.L. Parrain, J.C : Cintrat, A. Duchene, Synthesis, 1996, 1, 82-86. 114 Ali H. Al. Ha Kim, A. H. Haines, Tetr. Lett., 1982, 23(50), 5295-5298. 115 D. Grandjean, P. Pale, J. Chuche, Tetrahedron, 1993, 49(24), 5225-5226.