1 Palladium-catalyzed Coupling Reactions <strong>of</strong> Indoles 69 Piettre, S. Baltzer, Tetrahedron Lett. 1997, 38, 1197-1200; d) P. A. Tempest, R. W. Armstrong, J. Am. Chem. Soc. 1997, 119, 7607-7608. [46] T. Kasahara, Y. Kondo, Heterocycles 2006, 67, 95-100. [47] a) T. Ishiyama, K. Ishida, N. Miyaura, Tetrahedron 2001, 57, 9813-9816; b) T. Ishiyama, M. Murata, N. Miyaura, J. Org. Chem. 1995, 60, 7508-7510. [48] a) M. Murata, T. Oyama, S. Watanabe, Y. Masuda, J. Org. Chem. 2000, 65, 164-168; b) M. Murata, S. Watanabe, Y. Masuda, J. Org. Chem. 1997, 62, 6458-6459. [49] a) I. D. Hills, M. R. Netherton, G. C. Fu, Angew. Chem. Int. Ed. 2003, 42, 5749-5752; Angew. Chem. 2003, 115, 5927-5930; b) A. F. Littke, C. Dai, G. C. Fu J. Am. Chem. Soc. 2000, 122, 4020-4028. [50] a) M. Gallant, J. T. Link, S. J. Danishefsky, J. Org. Chem. 1993, 58, 343- 349; b) T. Kaneko, H. Wong, K. T. Okamoto, J. Clardy, Tetrahedron Lett. 1985, 26, 4015-4018. [51] a) For review <strong>of</strong> the medicinal chemistry <strong>of</strong> vinblastine, see: Antitumor Bisindole Alkaloids from Catharanthus roseus (L.). The Alkaloids; A. Brossi, M. Suffness, Eds.: Academic Press, Inc.; San Diego, 1990, Vol. 37, Chapter 3 <strong>and</strong> 4, pp. 133-204; b) G. H. Svoboda, N. Neuss, M. Gorman, J. Am. Pharm. Assoc. Sci. Ed. 1959, 48, 659-666; c) R. L. Noble, C. T. Beer, J. H. Cutts, Ann. N. Y. Acad. Sci. 1958, 76, 882-894. [52] P. D. Johnson, J-H. Sohn, V. H. Rawal, J. Org. Chem. 2006, 71, 7899- 7902. [53] E. R. Strieter, D. G. Blackmond, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 13978-13980. [54] a) S. Ghosal, R. Lochan, A. Y Kumar, R. Srivastava, Phytochemistry 1985, 24, 1825-1828; b) S. Ghosal, P. H. Rao, Y. Kumar, A. W. Frahm, Phytochemistry 1981, 20, 2003-2007. [55] U. V. Mentzel, D. Tanner, J. E. Tonder, J. Org. Chem. 2006, 71, 5807-5810. [56] a) O. Baudoin, M. Cesario, D. Guénard, F. Guéritte, J. Org. Chem. 2002, 67, 1199-1207; b) O. Baudoin, D. Guénard, F. Guéritte, J. Org. Chem. 2000, 65, 9268-9271. [57] a) R. Olivera, R. SanMartin, I. Tellitu, E. Domínguez, Tetrahedron 2002, 58, 3021-3037; b) R. Grigg, A. Teasdale, V. Sridharan, Tetrahedron Lett. 1991, 32, 3859-3862.
1 Palladium-catalyzed Coupling Reactions <strong>of</strong> Indoles 70 [58] P. Appukkuttan, E. Van der Eycken, W. Dehaen, Synlett 2003, 14, 1204- 1206; b) C. G. Hartung, A. Fecher, B. Chapell, V. Snieckus, Org. Lett. 2003, 5, 1899-1902. [59] J. P. Wolfe, R. A. Singer, B. H. Yang, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 9550-9561. [60] M., E. Zurita, E. Rosa, L. Muñoz, P. Lloyed-Williams, E. Giralt, J. Org. Chem. 2004, 69, 6812-6820; [61] a) C. Amatore, A. Jut<strong>and</strong>, Acc. Chem. Res. 2000, 33, 314-321; b) K. Matos, J. A. Soderquist, J. Org. Chem. 1998, 63, 461-470; c) M. Moreno Mañas, M. Pérez, R. Pleixats, J. Org. Chem. 1996, 61, 2346-2351; d) G. B. Smith, G. C. Dezeny, D. L. Hughes, A. O. King, T. R. Verhoeven, J. Org. Chem. 1994, 59, 8151-8156. [62] P. Fitton, E. A. Rick, J. Organomet. Chem. 1971, 28, 287-291. [63] a) D. Badone, M. Baroni, R. Cardamone, A. Lelmini, U. Guzzi, J. Org. Chem. 1997, 62, 7170-7173; b) R. W. Friesen, L. A. Trimble, Can. J. Chem. 2004, 82, 206-214. [64] A. N. Cammidge, K. V. L. Crepy, J. Org. Chem. 2003, 68, 6832-6835. [65] S. Ma, X. Jiang, X. Cheng, H. Hou, Adv. Synth. Catal. 2006, 348, 2114- 2124. [66] For reviews <strong>of</strong> natural products containing �-lactone, see: a) I. Martinez, A. E. Andrews, J. D. Emch, A. J. Ndakala, J. Wang, A. R. Howell, Org. Lett. 2003, 5, 399-402; b) H. W. Yang, D. Romo, Tetrahedron 1999, 55, 6403- 6434; c) C. Lowe, J. C. Vederas, Org. Prep. Proc. Int. 1995, 27, 305-346; d) A. Pommier, J. M. Pons, Synthesis 1995, 729-744; e) A. Pommier, J. M. Pons, Synthesis 1993, 441-459; f) R. L. Danheiser, Y. M. Choi, M. Menichincheri, E. J. Stoner, J. Org. Chem. 1993, 58, 322-327. [67] a) J. Marco-Contelles, Angew. Chem. Int. Ed. 2004, 43, 2198-2200; Angew. Chem. 2004, 116, 2248-2250; b) G. C. Fu, R. Shintani, Angew. Chem. Int. Ed. 2003, 42, 4082-4085; Angew. Chem. 2003, 115, 4216-4219; c) P. A. Magriotis, Angew. Chem. Int. Ed. 2001, 40, 4377-4379; Angew. Chem. 2001, 113, 4507-4509; d) Synthesis <strong>of</strong> �-Lactam Antibiotics: Chemistry, Biocatalysis <strong>and</strong> Process Integration, (Ed. A. Bruggink), Kluwer, Dordrecht, Netherl<strong>and</strong>s, 2001; e) I. Ojima, F. Delaloge, Chem. Soc. Rev. 1997, 26, 377-386.
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Table of Contents Preface .........
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List of Abbreviations Ac Acetyl aq
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Preface The search for drugs is an
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Synthesis of Potential 5-HT 6 Recep
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Synthesis of Potential 5-HT 6 Recep
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Synthesis of Indole-2,3-dicarboxyla
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8 7 N R N R OH CO2Et CO2Et OH indol
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Over the past years, we investigate
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Publikationen 1 Titanium-Catalyzed