RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
Synthesis 2012; 44(17): 2743-2753
DOI: 10.1055/s-0032-1316579
DOI: 10.1055/s-0032-1316579
paper
Synthetic Studies toward Ecteinascidin 743 (Trabectedin)
Authors
Weitere Informationen
Publikationsverlauf
Received: 01. Mai 2012
Accepted after revision: 31. Mai 2012
Publikationsdatum:
06. Juli 2012 (online)
Abstract
An alternative synthetic route to an intermediate in the synthesis of ecteinascidin 743 has been established by using a Pictet–Spengler reaction and a Friedel–Crafts type reaction.
Key words
alkaloids - anticancer drugs - Pictet–Spengler reaction - Friedel–Crafts reaction - total synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information (PDF)
-
References
- 1 Visiting researcher from Meiji Seika Pharma, Ltd
- 2 Rinehart K. Med. Res. Rev. 2000; 20: 1
- 3a Rinehart K, Holt T, Fregeau N, Stroh J, Keifer P, Sun F, Li L, Martin D. J. Org. Chem. 1990; 55: 4512
- 3b Wright A, Forleo D, Gunawardana G, Gunasekera S, Koehn F, Mcconnell O. J. Org. Chem. 1990; 55: 4508
- 3c Sakai R, Rinehart K, Guan Y, Wang A. Proc. Natl. Acad. Sci. U.S.A. 1992; 89: 11456
- 3d Sakai R, Jareserijman E, Manzanares I, Elipe M, Rinehart K. J. Am. Chem. Soc. 1996; 118: 9017
- 4a Pommier Y, Kohlhagen G, Bailly C, Waring M, Mazumder A, Kohn K. Biochemistry 1996; 35: 13303
- 4b Moore B, Seaman F, Hurley L. J. Am. Chem. Soc. 1997; 119: 5475
- 4c Moore B, Seaman F, Wheelhouse R, Hurley L. J. Am. Chem. Soc. 1998; 120: 2490
- 4d Moore B, Seaman F, Wheelhouse R, Hurley L. J. Am. Chem. Soc. 1998; 120: 9975
- 4e Seaman F, Hurley L. J. Am. Chem. Soc. 1998; 120: 13028
- 4f Takebayashi Y, Pourquier P, Yoshida A, Kohlhagen G, Pommier Y. Proc. Natl. Acad. Sci. U.S.A. 1999; 96: 7196
- 4g Zewail-Foote M, Hurley L. J. Med. Chem. 1999; 42: 2493
- 4h Garcia-Nieto R, Manzanares I, Cuevas C, Gago F. J. Am. Chem. Soc. 2000; 122: 7172
- 4i Garcia-Nieto R, Manzanares I, Cuevas C, Gago F. J. Med. Chem. 2000; 43: 4367
- 4j Takebayashi Y, Pourquier P, Zimonjic D, Nakayama K, Emmert S, Ueda T, Urasaki Y, Kanzaki A, Akiyama S, Popescu N, Kraemer K, Pommier Y. Nat. Med. 2001; 7: 961
- 4k Zewail-Foote M, Li V, Kohn H, Bearss D, Guzman M, Hurley L. Chem. Biol. 2001; 8: 1033
- 4l Zewail-Foote M, Hurley L. J. Am. Chem. Soc. 2001; 123: 6485
- 4m Kanzaki A, Takebayashi Y, Ren X, Miyashita H, Mori S, Akiyama S, Pommier Y. Mol. Cancer Ther. 2002; 1: 1327
- 4n Marco E, Garcia-Nieto R, Mendieta J, Manzanares I, Cuevas C, Gago F. J. Med. Chem. 2002; 45: 871
- 4o Gajate C, An F, Mollinedo F. J. Biol. Chem. 2002; 277: 41580
- 4p Minuzzo M, Ceribelli M, Pitarque-Marti M, Borrelli S, Erba E, Disilvio A, D’Incalci M, Mantovani R. Mol. Pharmacol. 2005; 68: 1496
- 4q Marco E, David-Cordonnier M.-H, Bailly C, Cuevas C, Gago F. J. Med. Chem. 2006; 49: 6925
- 4r Soares DG, Escargueil AE, Poindessous V, Sarasin A, De Gramont A, Bonatto D, Pegas Henriques JA, Larsen AK. Proc. Natl. Acad. Sci. U.S.A. 2007; 104: 13062
- 5 Zelek L, Yovine A, Brain E, Turpin F, Taamma A, Riofrio M, Spielmann M, Jimeno J, Misset JL. Brit. J. Cancer 2006; 94: 1610
- 6a Corey E, Gin D, Kania R. J. Am. Chem. Soc. 1996; 118: 9202
- 6b Corey E, Gin D. Tetrahedron Lett. 1996; 37: 7163
- 7a Endo A, Kann T, Fukuyama T. Synlett 1999; 1103
- 7b Endo A, Yanagisawa A, Abe M, Tohma S, Kan T, Fukuyama T. J. Am. Chem. Soc. 2002; 124: 6552
- 8 Chen J, Chen X, Bois-Choussy M, Zhu J. J. Am. Chem. Soc. 2006; 128: 87
- 9 Fishlock D, Williams RM. J. Org. Chem. 2008; 73: 9594
- 10 Zheng S, Chan C, Furuuchi T, Wright B, Zhou B, Guo J, Danishefsky S. Angew. Chem. Int. Ed. 2006; 45: 1754
- 11 Enomoto T, Yasui Y, Takemoto Y. J. Org. Chem. 2010; 75: 4876
- 12a Saito N, Kamayachi H, Tachi M, Kubo A. Heterocycles 1999; 51: 9
- 12b Saito N, Tachi M, Seki R, Kamayachi H, Kubo A. Chem. Pharm. Bull. 2000; 48: 1549
- 12c Zhou B, Guo J, Danishefsky S. Org. Lett. 2002; 4: 43
- 12d De Paolis M, Chiaroni A, Zhu J. Chem. Commun. 2003; 2896
- 12e Gonzalez J, Salazar L, De La Cuesta E, Avendano C. Tetrahedron 2005; 61: 7447
- 12f Ceballos P, Perez M, Cuevas C, Francesch A, Manzanares I, Echavarren A. Eur. J. Org. Chem. 2006; 1926
- 12g Chandrasekhar S, Reddy NR, Rao YS. Tetrahedron 2006; 62: 12098
- 12h Vincent G, Lane JW, Williams RM. Tetrahedron Lett. 2007; 48: 3719
- 12i Chang YA, Sun TH, Chiang MY, Lu PJ, Huang YT, Liang LC, Ong CW. Tetrahedron 2007; 63: 8781
- 13 Cuevas C, Perez M, Martin M, Chicharro J, Fernandez-Rivas C, Flores M, Francesch A, Gallego P, Zarzuelo M, De La Calle F, Garcia J, Polanco C, Rodriguez I, Manzanares I. Org. Lett. 2000; 2: 2545
- 14 Saito N, Tachi M, Seki R, Sugawara Y, Takeuchi E, Kubo A. Synth. Commun. 2000; 30: 2407
- 15 Schmidt U, Lieberknecht A, Wild J. Synthesis 1984; 53
- 16 Burk MJ, Feaster JE, Nugent WA, Harlow RL. J. Am. Chem. Soc. 1993; 115: 10125
Reference Ris Wihthout Link
- 17 Conversion of the protective group facilitated the isolation of 18
- 18 Nishida A, Nakagawa M, Uchida H, Ono K, Kimura Y, Yamabe M, Watanabe T, Tsuji R, Akiba M, Terada Y, Nagaki D, Ban S, Miyashita N, Kano T, Theeraladanon C, Hatakeyama K, Arisawa M. Heterocycles 2003; 59: 721
- 19a Tohma S, Endo A, Kan T, Fukuyama T. Synlett 2001; 1179
- 19b Tohma S, Rikimaru K, Endo A, Shimamoto K, Kan T, Fukuyama T. Synthesis 2004; 909
- 19c Nakata H, Imai T, Yokoshima S, Fukuyama T. Heterocycles 2008; 76: 747
- 20 Ager D, Cooper N, Cox G, Garrohelion F, Harwood L. Tetrahedron: Asymmetry 1996; 7: 2563
- 21 Harada H, Hirokawa Y, Suzuki K, Hiyama Y, Oue M, Kawashima H, Kato H, Yoshida N, Furutani Y, Kato S. Chem. Pharm. Bull. 2005; 53: 184
- 22 Since the phenolic hydroxy group was essential for the regioselective addition in the Friedel–Crafts type arylation, the methyl group was introduced at this stage
- 23 Hayashi T, Konishi M, Kobori Y, Kumada M, Higuchi T, Hirotsu K. J. Am. Chem. Soc. 1984; 106: 158