Total Synthesis of Tryprostatins A and B†
Correction(s) for this article
-
Berichtigung: Total Synthesis of Tryprostatins A and B
- Volume 126Issue 34Angewandte Chemie
- pages: 8953-8953
- First Published online: August 13, 2014
Takayuki Yamakawa
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694
Search for more papers by this authorEiji Ideue
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694
Search for more papers by this authorJun Shimokawa
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694
Search for more papers by this authorCorresponding Author
Prof. Dr. Tohru Fukuyama
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694Search for more papers by this authorTakayuki Yamakawa
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694
Search for more papers by this authorEiji Ideue
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694
Search for more papers by this authorJun Shimokawa
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694
Search for more papers by this authorCorresponding Author
Prof. Dr. Tohru Fukuyama
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan), Fax: (+81) 358-028-694Search for more papers by this authorFinancial support for this research was provided by Grants-in-Aid (21790009 and 20002004) from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
Graphical Abstract
Gezähmte Radikale: Die Entwicklung verlässlicher Bedingungen für die radikalvermittelte Bildung von Indolen führte zur effizienten Synthese der Tryprostatine A und B. Mit dem Radikalstarter 2,2′-Azobis(4-methoxy-2,4-dimethylvaleronitril) gelang die radikalische Cyclisierung schon bei 30 °C, sodass die Bildung von Nebenprodukten unterdrückt war.
Supporting Information
Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors.
Filename | Description |
---|---|
ange_201004963_sm_miscellaneous_information.pdf5.8 MB | miscellaneous_information |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aC.-B. Cui, H. Kakeya, G. Okada, R. Onose, M. Ubukata, I. Takahashi, K. Isono, H. Osada, J. Antibiot. 1995, 48, 1382–1384;
- 1bC.-B. Cui, H. Kakeya, G. Okada, R. Onose, H. Osada, J. Antibiot. 1996, 49, 527–533;
- 1cC.-B. Cui, H. Kakeya, H. Osada, J. Antibiot. 1996, 49, 534–540.
- 2
- 2aT. Usui, M. Kondoh, C.-B. Cui, T. Mayumi, H. Osada, Biochem. J. 1998, 333, 543–548;
- 2bM. Kondoh, T. Usui, T. Mayumi, H. Osada, J. Antibiot. 1998, 51, 801–804;
- 2cH. Woehlecke, H. Osada, A. Herrmann, H. Lage, Int. J. Cancer 2003, 107, 721–728.
- 3
- 3aK. M. Depew, S. J. Danishefsky, N. Rosen, L. Sepp-Lorenzino, J. Am. Chem. Soc. 1996, 118, 12463–12464;
- 3bJ. M. Schkeryantz, J. C. G. Woo, P. Siliphaivanh, K. M. Depew, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 11964–11975;
- 3cT. Gan, J. M. Cook, Tetrahedron Lett. 1997, 38, 1301–1304;
- 3dT. Gan, R. Liu, P. Yu, S. Zhao, J. M. Cook, J. Org. Chem. 1997, 62, 9298–9304;
- 3eS. Zhao, T. Gan, P. Yu, J. M. Cook, Tetrahedron Lett. 1998, 39, 7009–7012;
- 3fA. S. Cardoso, A. M. Lobo, S. Prabhakar, Tetrahedron Lett. 2000, 41, 3611–3613;
- 3gB. Wang, L. Chen, K. Kim, Tetrahedron Lett. 2001, 42, 1463–1466;
- 3hE. Caballero, C. Avendaño, J. C. Menéndez, J. Org. Chem. 2003, 68, 6944–6951;
- 3iA. S. P. Cardoso, M. M. B. Marques, N. Srinivasan, S. Prabhakar, A. M. Lobo, H. S. Rzepa, Org. Biomol. Chem. 2006, 4, 3966–3972.
- 4For syntheses of analogues, see:
- 4aJ. F. Sanz-Cervera, E. M. Stocking, T. Usui, H. Osada, R. M. Williams, Bioorg. Med. Chem. 2000, 8, 2407–2415;
- 4bH. Wang, T. Usui, H. Osada, A. Ganesan, J. Med. Chem. 2000, 43, 1577–1585;
- 4cC. Ma, X. Liu, X. Li, J. Flippen-Anderson, S. Yu, J. M. Cook, J. Org. Chem. 2001, 66, 4525–4542;
- 4dS. Zhao, K. S. Smith, A. M. Deveau, C. M. Dieckhaus, M. A. Johnson, T. L. Macdonald, J. M. Cook, J. Med. Chem. 2002, 45, 1559–1562;
- 4eH. D. Jain, C. Zhang, S. Zhou, H. Zhou, J. Ma, X. Liu, X. Liao, A. M. Deveau, C. M. Dieckhaus, M. A. Johnson, K. S. Smith, T. L. Macdonald, H. Kakeya, H. Osada, J. M. Cook, Bioorg. Med. Chem. 2008, 16, 4626–4651;
- 4fJ. Wagger, J. Svete, B. Stanovnik, Synthesis 2008, 1436–1442.
- 5
- 5aT. Fukuyama, X. Chen, G. Peng, J. Am. Chem. Soc. 1994, 116, 3127–3128;
- 5bS. Kobayashi, T. Fukuyama, J. Heterocycl. Chem. 1998, 35, 1043–1055;
- 5cS. Kobayashi, G. Peng, T. Fukuyama, Tetrahedron Lett. 1999, 40, 1519–1522;
- 5dS. Kobayashi, T. Ueda, T. Fukuyama, Synlett 2000, 883–886;
- 5eH. Tokuyama, M. Watanabe, Y. Hayashi, T. Kurokawa, G. Peng, T. Fukuyama, Synlett 2001, 1403–1406;
- 5fH. Tokuyama, T. Fukuyama, Chem. Rec. 2002, 2, 37–45;
- 5gS. Sumi, K. Matsumoto, H. Tokuyama, T. Fukuyama, Org. Lett. 2003, 5, 1891–1893;
- 5hS. Sumi, K. Matsumoto, H. Tokuyama, T. Fukuyama, Tetrahedron 2003, 59, 8571–8587.
- 6
- 6aH. Tokuyama, T. Yamashita, M. T. Reding, Y. Kaburagi, T. Fukuyama, J. Am. Chem. Soc. 1999, 121, 3791–3792;
- 6bM. T. Reding, T. Fukuyama, Org. Lett. 1999, 1, 973–976;
- 6cM. T. Reding, Y. Kaburagi, H. Tokuyama, T. Fukuyama, Heterocycles 2002, 56, 313–330;
- 6dS. Yokoshima, T. Ueda, S. Kobayashi, A. Sato, T. Kuboyama, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2002, 124, 2137–2139;
- 6eS. Yokoshima, T. Ueda, S. Kobayashi, A. Sato, T. Kuboyama, H. Tokuyama, T. Fukuyama, Pure Appl. Chem. 2003, 75, 29–38;
- 6fT. Kuboyama, S. Yokoshima, H. Tokuyama, T. Fukuyama, Proc. Natl. Acad. Sci. USA 2004, 101, 11966–11970;
- 6gY. Kaburagi, H. Tokuyama, T. Fukuyama, J. Am. Chem. Soc. 2004, 126, 10246–10247;
- 6hT. Miyazaki, S. Yokoshima, S. Simizu, H. Osada, H. Tokuyama, T. Fukuyama, Org. Lett. 2007, 9, 4737–4740.
- 7
- 7aA. Dondoni, D. Perrone in Org. Synth. Coll. Vol. 10 (Ed.: ), Wiley, Hoboken, NJ, 2004, pp. 320–326;
- 7bP. Garner, J. M. Park, Org. Synth. Coll. Vol. 9 (Ed.: ), Wiley, Hoboken, NJ, 1998, pp. 300–306.
- 8J. Erdsack, N. Krause, Synthesis 2007, 3741–3750.
- 9C. A. Brown, V. K. Ahuja, J. Chem. Soc. Chem. Commun. 1973, 553–554.
- 10
- 10aK. R. Buszek, N. Brown, J. Org. Chem. 2007, 72, 3125–3128;
- 10bA. G. Myers, B. Zheng, M. Movassaghi, J. Org. Chem. 1997, 62, 7507–7507.
- 11M. H. P. J. Aerssens, R. van der Heiden, M. Heus, L. Brandsma, Synth. Commun. 1990, 20, 3421–3425.
- 12S. Minegishi, S. Kobayashi, H. Mayr, J. Am. Chem. Soc. 2004, 126, 5174–5181.
- 13
- 13aY. Kita, K. Gotanda, K. Murata, M. Suemura, A. Sano, T. Yamaguchi, M. Oka, M. Matsugi, Org. Process Res. Dev. 1998, 2, 250–254;
- 13bY. Kita, A. Sano, T. Yamaguchi, M. Oka, K. Gotanda, M. Matsugi, J. Org. Chem. 1999, 64, 675–678;
- 13cY. Kita, A. Sano, T. Yamaguchi, M. Oka, K. Gotanda, M. Matsugi, Tetrahedron Lett. 1997, 38, 3549–3552.
- 14Dihydroquinoline intermediate underwent further reduction to afford tetrahydroquinoline 19.
- 15
- 15aA. López-Cobeñas, P. Cledera, J. D. Sánchez, P. López-Alvarado, M. T. Ramos, C. Avendaño, J. C. Menéndez, Synthesis 2005, 3412–3422;
- 15bV. H. Rawal, M. P. Cava, Tetrahedron Lett. 1985, 26, 6141–6142.
- 16See the Supporting Information for a detailed description of the preparation of 28.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.