The efficient synthesis of natural products, drugs, and materials with economical and ecological advantages is a very important goal in modern synthetic chemistry. In such an approach, toxic substrates as well as reagents have to be avoided, the amount of waste has to be reduced, and the exploitation of our resources has to be diminished. In this respect, the use of catalytic processes is highly advantageous; however, even more beneficial is the combination of several catalytic processes either in a sequential or, more efficiently, in a domino mode. In this article, the synthesis of several natural products, drugs, and materials is described, employing multiple Pd-catalyzed processes either in a sequential or a domino fashion. Based on a double-Heck reaction developed by us for the preparation of estradiol, the efficient synthesis of the highly potent contraceptive desogestrel is discussed; for the synthesis of α-tocopherol and diversonol an enantioselective domino-Wacker/Heck reaction was utilized, whereas in the case of diversonol, a domino-Wacker/carbonylation was even more effective, and several molecular switches containing a helical tetrasubstituted double bond were prepared employing a domino-carbopalladation/Stille reaction. Finally, acenaphthylenes could be obtained by a domino-carbopalladation/C–H-activation.
Conference
International Conference on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-15), International Symposium on Organometallic Chemistry Directed Toward Organic Synthesis, OMCOS, Organometallic Chemistry Directed Toward Organic Synthesis, 15th, Glasgow, UK, 2009-07-26–2009-07-31
References
1a 10.1002/ange.200804883, H. Ishikawa, T. Suzuki, Y. Hayashi. Angew. Chem.121, 1330 (2009).Search in Google Scholar
1b 10.1002/anie.200804883, H. Ishikawa, T. Suzuki, Y. Hayashi. Angew. Chem., Int. Ed.48, 1304 (2009).Search in Google Scholar PubMed
2a L. F. Tietze, G. Brasche, K. Gericke. Domino Reactions in Organic Synthesis, Wiley-VCH, Weinheim (2006).10.1002/9783527609925Search in Google Scholar
2b 10.1002/ange.19931050204, L. F. Tietze, U. Beifuss. Angew. Chem.105, 137 (1993).Search in Google Scholar
2c 10.1002/anie.199301313, L. F. Tietze, U. Beifuss. Angew. Chem., Int. Ed. Engl.32, 131 (1993).Search in Google Scholar
2d 10.1021/cr950027e, L. F. Tietze. Chem. Rev.96, 115 (1995).Search in Google Scholar PubMed
2e L. F. Tietze, N. Rackelmann. In Multicomponent Reactions, J. Zhu (Ed.), Wiley-VCH, Weinheim (2005).Search in Google Scholar
2f L. F. Tietze, L. Levy. In The Mizoroki-Heck Reaction, M. Oestreich (Ed.), Wiley-VCH, Chichester (2009).Search in Google Scholar
2g L. F. Tietze, D. A. Spiegl, C. C. Brazel. In Experiments in Green and Sustainable Chemistry, H. W. Roesky, D. K. Kennepohl (Eds.), Wiley-VCH, Weinheim (2009).Search in Google Scholar
2h L. F. Tietze, A. Düfert. In Catalytic Asymmetric Conjugate Reactions, A. Cordóva (Ed.), Wiley-VCH, Weinheim (2010).Search in Google Scholar
2i 10.1351/pac200476111967, L. F. Tietze, N. Rackelmann. Pure Appl. Chem.76, 1967 (2004).Search in Google Scholar
2j 10.1351/pac200779040629, L. F. Tietze, T. Kinzel. Pure Appl. Chem.79, 629 (2007).Search in Google Scholar
2k 10.1021/ar800170y, L. F. Tietze, T. Kinzel, C. Brazel. Acc. Chem. Res.42, 367 (2009).Search in Google Scholar PubMed
3a 10.1002/ange.200461432, A. C. Frisch, M. Beller. Angew. Chem.117, 680 (2005).Search in Google Scholar
3b 10.1002/anie.200461432, A. C. Frisch, M. Beller. Angew. Chem., Int. Ed.44, 674 (2005).Search in Google Scholar
3c 10.1002/ange.200803611, A. Rudolph, M. Lautens. Angew. Chem.121, 2694 (2009).Search in Google Scholar
3d 10.1002/anie.200803611, A. Rudolph, M. Lautens. Angew. Chem., Int. Ed.48, 2656 (2009).Search in Google Scholar
3e 10.1021/ar800148f, G. C. Fu. Acc. Chem. Res.41, 1555 (2008).Search in Google Scholar
3f 10.1021/cr030700x, L. F. Tietze, I. Hiriyakkanavar, H. P. Bell. Chem. Rev.104, 3453 (2004).Search in Google Scholar
4a 10.1002/anie.199622591, L. F. Tietze, T. Nöbel, M. Spescha. Angew. Chem., Int. Ed. Engl.35, 2259 (1996).Search in Google Scholar
4b 10.1021/ja981539o, L. F. Tietze, T. Nöbel, M. Spescha. J. Am. Chem. Soc.120, 8971 (1998).Search in Google Scholar
4c 10.1002/1099-0690(200105)2001:9<1619::AID-EJOC1619>3.0.CO;2-T, L. F. Tietze, S. Petersen. Eur. J. Org. Chem. 1619 (2001).Search in Google Scholar
5 10.1002/chem.200700182, L. F. Tietze, I. Krimmelbein. Chem.—Eur. J.14, 1541 (2008).Search in Google Scholar
6 10.1002/chem.200800967, L. F. Tietze, D. A. Spiegl, F. Stecker, J. Major, C. Raith, C. Grosse. Chem.—Eur. J.14, 8956 (2008).Search in Google Scholar
7a 10.1002/ange.200461629, L. F. Tietze, K. M. Sommer, J. Zinngrebe, F. Stecker. Angew. Chem.117, 262 (2005).Search in Google Scholar
7b 10.1002/anie.200461629, L. F. Tietze, K. M. Sommer, J. Zinngrebe, F. Stecker. Angew. Chem., Int. Ed.44, 257 (2005).Search in Google Scholar
7c 10.1002/chem.200600849, L. F. Tietze, F. Stecker, J. Zinngrebe, K. M. Sommer. Chem.—Eur. J.12, 8770 (2006).Search in Google Scholar
8 10.1021/ja906260x, L. F. Tietze, A. Düfert, F. Lotz, L. Sölter, K. Oum, T. Lenzer, T. Beck, R. Herbst-Irmer. J. Am. Chem. Soc.131, 17879 (2009).Search in Google Scholar
9a 10.1002/anie.200601003, L. F. Tietze, G. Brasche, C. Stadler, A. Grube, N. Böhnke. Angew. Chem., Int. Ed.45, 5015 (2006).Search in Google Scholar
9b 10.1002/chem.200700113, L. F. Tietze, G. Brasche, A. Grube, N. Böhnke, C. Stadler. Chem.—Eur. J.13, 4396 (2007).Search in Google Scholar
10a 10.1002/ange.19971091027, L. F. Tietze, H. Schirok. Angew. Chem.109, 1159 (1997).Search in Google Scholar
10b 10.1002/anie.199711241, L. F. Tietze, H. Schirok. Angew. Chem., Int. Ed. Engl.36, 1124 (1997).Search in Google Scholar
10c 10.1021/ja991650+, L. F. Tietze, H. Schirok. J. Am. Chem. Soc.121, 10264 (1999).Search in Google Scholar
10d 10.1002/(SICI)1521-3765(20000204)6:3<510::AID-CHEM510>3.0.CO;2-H, L. F. Tietze, H. Schirok, M. Wöhrmann. Chem.—Eur. J.6, 510 (2000).Search in Google Scholar
10e 10.1002/1099-0690(200007)2000:13<2433::AID-EJOC2433>3.0.CO;2-G, L. F. Tietze, H. Schirok, M. Wöhrmann, K. Schrader. Eur. J. Org. Chem. 2433 (2000).Search in Google Scholar
10f 10.1016/j.tet.2007.03.020, L. F. Tietze, H. Braun, P. L. Steck, S. A. A. El Bialy, N. Tölle, A. Düfert. Tetrahedron63, 6437 (2007).Search in Google Scholar
11 L. F. Tietze, F. Stecker. Unpublished material.Search in Google Scholar
12 10.1002/chem.200701676, L. F. Tietze, T. Redert, H. P. Bell, S. Hellkamp, L. M. Levy. Chem.—Eur. J.14, 2527 (2008).Search in Google Scholar
13a 10.1021/ja991016w, J. H. Rigby, N. C. Warshakoon, A. J. Payen. J. Am. Chem. Soc.121, 8237 (1999).Search in Google Scholar
13b 10.1039/np9941100607, F. Zeelen. Nat. Prod. Rep.11, 607 (1994).Search in Google Scholar
14a K. M. D. Islam, M. Dilcher, C. Thurow, C. Vock, I. K. Krimmelbein, L. F. Tietze, V. Gonzalez, H. Zhao, C. Gatz. PEDS22, 45 (2009).10.1093/protein/gzn067Search in Google Scholar
14b 10.1055/s-0029-1216810, L. F. Tietze, C. A. Vock, I. K. Krimmelbein, L. Nacke. Synthesis 2040 (2009).Search in Google Scholar
14c 10.1002/chem.200701600, L. F. Tietze, C. A. Vock, I. K. Krimmelbein, J. M. Wiegand, L. Nacke, T. Ramachandar, K. M. D. Islam, C. Gatz. Chem.—Eur. J.14, 3670 (2008).Search in Google Scholar
15a 10.1002/ange.19951071708, W. A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer. Angew. Chem.107, 1989 (1995).Search in Google Scholar
15b 10.1002/anie.199518441, W. A. Herrmann, C. Broßmer, K. Öfele, C.-P. Reisinger, T. Priermeier, M. Beller, H. Fischer. Angew. Chem., Int. Ed. Engl.34, 1844 (1995).Search in Google Scholar
15c 10.1002/chem.19970030823, W. A. Herrmann, C. Broßmer, K. Öfele, C. P. Reisinger, T. Priermeier, M. Beller, H. Fischer. Chem.—Eur. J.3, 1357 (1997).Search in Google Scholar
16 10.1016/S0040-4020(00)01144-3, Y. Kashiwada, K. Yamazaki, Y. Ikeshiro, T. Yamagashi, T. Fujioka, K. Mihashi, K. Mizuki, L. K. Cosentino, K. Fowke, S. L. Morris-Natschke, K.-H. Lee. Tetrahedron57, 1559 (2001).Search in Google Scholar
17 10.1002/ardp.19062440411, F. Kraft. Arch. Pharm.244, 336 (1906).Search in Google Scholar
18a 10.1002/hlca.19520350632, A. Stoll, J. Renz, A. Brack. Helv. Chim. Acta35, 2022 (1952).Search in Google Scholar
18b I. Kurobane, S. Iwahashi, A. Fukuda. Drugs Exp. Clin. Res.13, 339 (1987).Search in Google Scholar
18c F. McPhee, P. S. Caldera, G. W. Bemis, A. F. McDonagh, I. D. Kuntz. Biochem. J.320, 681 (1996).Search in Google Scholar
19 Racemic approaches.Search in Google Scholar
19a 10.1002/anie.200802632, K. C. Nicolaou, A. Li. Angew. Chem., Int. Ed.47, 6579 (2008).Search in Google Scholar PubMed PubMed Central
19b C. F. Nising, A. Friedrich, S. Bräse. Synlett 2987 (2007).10.1055/s-2007-992365Search in Google Scholar
19c 10.1002/chem.200501485, C. F. Nising, U. K. Ohnemüller, A. Friedrich, B. Lesch, J. Steiner, H. Schnöckel, M. Nieger, S. Bräse. Chem.—Eur. J.12, 3647 (2006).Search in Google Scholar PubMed
19d 10.1002/ejoc.200500887, U. K. Ohnemüller, C. F. Nising, M. Nieger, S. Bräse. Eur. J. Org. Chem. 1535 (2006).Search in Google Scholar
19e 10.1002/ange.200502913, C. F. Nising, U. K. Ohnemüller, S. Bräse. Angew. Chem.118, 313 (2006).Search in Google Scholar
19f 10.1002/anie.200502913, C. F. Nising, U. K. Ohnemüller, S. Bräse. Angew. Chem., Int. Ed.45, 307 (2006).Search in Google Scholar PubMed
19g 10.1055/s-2005-917109, Y.-L. Shi, M. Shi. Synlett 2623 (2005).Search in Google Scholar
19h K. Y. Lee, J. M. Kim, J. N. Kim. Bull. Korean Chem. Soc.24, 17 (2003).Search in Google Scholar
19i 10.1039/a700375g, C. D. Gabbutt, J. D. Hepworth, M. W. J. Urquhart, L. M. Vazquez de Miguel. J. Chem. Soc., Perkin Trans. 1 1819 (1997).Search in Google Scholar
19j 10.1002/cber.19731060417, B. Franck, J. Stöckigt, U. Zeidler, G. Franckowiak. Chem. Ber.106, 1198 (1973).Search in Google Scholar
20 Enantioselective approaches.Search in Google Scholar
20a U. K. Ohnemüller, C. F. Nising, A. Encinas, S. Bräse. Synthesis 2175 (2007).10.1055/s-2007-983761Search in Google Scholar
20b 10.1016/j.tetlet.2007.01.094, R. Rios, H. Sundén, I. Ibrahem, A. Córdova. Tetrahedron Lett.48, 2181 (2007).Search in Google Scholar
21a 10.1016/S0040-4020(02)01584-3, H. Hocke, Y. Uozumi. Tetrahedron59, 619 (2003).Search in Google Scholar
21b H. Hocke, Y. Uozumi. Synlett 2049 (2002).10.1055/s-2002-35603Search in Google Scholar
21c 10.1021/jo982104m, Y. Uozumi, H. Kyota, K. Kato, M. Ogasawara, T. Hayashi. J. Org. Chem.64, 1620 (1999).Search in Google Scholar PubMed
21d 10.1021/jo980245i, Y. Uozumi, K. Kato, T. Hayashi. J. Org. Chem.63, 5071 (1998).Search in Google Scholar
21e 10.1021/ja9701366, Y. Uozumi, K. Kato, T. Hayashi. J. Am. Chem. Soc.119, 5063 (1997).Search in Google Scholar
21f 10.1021/jo9713619, M. B. Andrus, D. Asgari, J. A. Sclafani. J. Org. Chem.62, 9365 (1997).Search in Google Scholar
21g 10.1016/0957-4166(96)00193-0, Y. Uozumi, H. Kyota, E. Kishi, K. Kitayama, T. Hayashi. Tetrahedron: Asymmetry7, 1603 (1996).Search in Google Scholar
21h 10.1021/jo00088a066, T. D. Nelson, A. I. Meyers. J. Org. Chem.59, 2655 (1994).Search in Google Scholar
22 R. Noyori. Green Chem.5, G37 (2003).10.1039/b305339nSearch in Google Scholar
23a 10.3987/COM-07-S(W)67, L. F. Tietze, J. Zinngrebe, D. A. Spiegl, F. Stecker. Heterocycles74, 473 (2007).Search in Google Scholar
23b 10.3987/COM-08-S(F)91, L. F. Tietze, A. Heins, M. Soleiman-Beigi, C. Raith. Heterocycles77, 1123 (2008).Search in Google Scholar
23c 10.3987/COM-06-S(W)24, L. F. Tietze, K. F. Wilckens, S. Yilmaz, F. Stecker, J. Zinngrebe. Heterocycles70, 309 (2006).Search in Google Scholar
24a V. Balzani, M. Venturi, A. Credi. Molecular Devices and Machines: A Journey into the Nanoworld, Wiley-VCH, Weinheim (2003).Search in Google Scholar
24b Special issue on “Molecular machines”: Acc. Chem. Res.34, 409 (2001).10.1021/ar0100881Search in Google Scholar
25a B. L. Feringa (Ed.). Molecular Switches, Wiley-VCH, Weinheim (2001).10.1002/3527600329Search in Google Scholar
25b J. C. Crano, R. J. Guglielmetti. Organic Photochromic and Thermochromic Compounds, Vols. 1–3, Springer, New York (1999).Search in Google Scholar
25c 10.1021/cr9900228, B. L. Feringa, R. A. van Delden, N. Koumura, E. M. Geertsema. Chem. Rev.100, 1789 (2000).Search in Google Scholar PubMed
25d 10.1002/ange.200702197, Y.-L. Huang, W.-C. Hung, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu. Angew. Chem.119, 6749 (2007).Search in Google Scholar
25e 10.1002/anie.200702197, Y.-L. Huang, W.-C. Hung, C.-C. Lai, Y.-H. Liu, S.-M. Peng, S.-H. Chiu. Angew. Chem., Int. Ed.46, 6629 (2007).Search in Google Scholar
26a 10.1021/jo070394d, B. L. Feringa. J. Org. Chem.72, 6635 (2007).Search in Google Scholar
26b 10.1021/ja00444a046, B. L. Feringa, H. Wynberg. J. Am. Chem. Soc.99, 602 (1997).Search in Google Scholar
26c 10.1016/S0957-4166(00)80349-3, W. F. Jager, B. de Lange, A. M. Schoevaars, B. L. Feringa. Tetrahedron: Asymmetry4, 1481 (1993).Search in Google Scholar
27a 10.1021/ja971570a, K. Matsumura, S. Hashiguchi, T. Ikariya, R. Noyori. J. Am. Chem. Soc.119, 8738 (1997).Search in Google Scholar
27b 10.1002/ange.19971090333, K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori. Angew. Chem.109, 297 (1997).Search in Google Scholar
27c 10.1002/anie.199702851, K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori. Angew. Chem., Int. Ed. Engl.36, 285 (1997).Search in Google Scholar
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