The fused heterocyclic indolizinoquinolinone system is a key structural feature of several highly bioactive alkaloids, including camptothecin. Camptothecin has been efficiently obtained by a three- or four-component domino Knoevenagel / hetero-Diels–Alder reaction of aldehyde, Meldrum's acid, and enol ether in the presence or absence of alcohol, followed by reductive cleavage of the amine protecting group. The obtained products were further transformed along several different routes leading to camptothecin.
Similar content being viewed by others
References
(a) Bacherikov, V. A.; Tsai, T.-J.; Chang, J-Y.; Chou, T.-C.; Lee, R.-Z.; Su, T.-L. Eur. J. Org. Chem. 2006, 19, 4490. (b) Dai, W.; Petersen, J. L.; Wang, K. K. Org. Lett. 2006, 8, 4665. (c) Nakagawa, M.; Okajima, Y.; Kobayashi, K.; Asaka, T.; Hino, T. Heterocycles 1975, 3, 799.
(a) Thomas, C. J.; Rahier, N. J.; Hecht, S. M. Bioorg. Med. Chem. 2004, 12, 1585. (b) Li, Q.-Y.; Zu, Y.-G.; Shi, R.-Z.; Yao, L.-P. Curr. Med. Chem. 2006, 13, 2021. (c) Wall, M. E.; Wani, M. C.; Cook, C. E.; Palmer, K. H.; McPhail, A. T.; Sim, G. A. J. Am. Chem. Soc. 1966, 88, 3888.
Pommier, Y. Nat. Rev. Cancer 2006, 6, 789.
(a) Pommier, Y.; Leo, E.; Zhang, H.; Marchand, C. Chem. Biol. 2010, 17, 421. (b) Pommier, Y. ACS Chem. Biol. 2013, 8, 82. (c) O'Dwyer, P. J.; Catalano, R. B. J. Clin. Oncol. 2006, 24, 4534. (d) Jiang, P.; Mukhtavavam, R.; Chao, Y.; Bharati, I. S.; Fogal, V.; Pastorino, S.; Cong, X.; Nomura, N.; Gallagher, M.; Abbasi, T.; Vali, S.; Pingle, S. C.; Makale, M.; Kesari, S. J. Transl. Med. 2014, 12, 13.
(a) Moertel, C. G.; Schutt, A. J.; Reitemeir, R. J.; Hahn, R. G. Cancer Chemother. Rep. 1972, 56, 95. (b) Yu, M. Mol. Med. Rep. 2014, 9, 249. (c) Beaudet, A. L. Nature 2011, 481, 150. (d) Herzog, T. J. Oncologist 2002, 7, 3. (e) Garcia-Carbonero, R.; Supko, J. G. Clin. Cancer Res. 2002, 8, 641.
(a) Hsiang, Y.-H.; Hertzberg, R.; Hecht, S.; Liu, L. F. J. Biol. Chem. 1985, 260, 14873. (b) Hsiang, Y.-H.; Liu, L. F.; Wall, M. E.; Wani, M. C.; Nicholas, A. W.; Manikumar, G.; Kirschenbaum, S.; Silber, R.; Potmesil, M. Cancer Res. 1989, 49, 4385. (c) Covey, J. M.; Jaxel, C.; Kohn, K. W.; Pommier, Y. Cancer Res. 1989, 49, 5016. (d) Verma, R. P.; Hansch, C. Chem. Rev. 2009, 109, 213.
(a) Tietze, L. F.; Brasche, G.; Gericke, K. M. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, 2006. (b) Tietze, L. F. Chem. Rev. 1996, 96, 115. (c) Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137; Angew. Chem., Int. Ed. Engl. 1993, 32, 131.
(a) Tietze, L. F.; Düfert, A.; Lotz, F.; Sölter, L.; Oum, K.; Lenzer, T.; Beck, T.; Herbst-Irmer, R. J. Am. Chem. Soc. 2009, 131, 17879. (b) Tietze, L. F.; Duefert, S.-C.; Clerc, J.; Bischoff, M.; Maaß, C.; Stalke, D. Angew. Chem. 2013, 125, 3273; Angew. Chem., Int. Ed. 2013, 52, 3191. (c) Tietze, L. F.; Eichhorst, C. Heterocycles 2015, 90, 919. (d) Tietze, L. F.; Waldecker, B.; Ganapathy, D.; Eichhorst, C.; Lenzer, T.; Oum, K.; Reichmann, S. O.; Stalke, D. Angew. Chem. 2015, 127, 10457; Angew. Chem., Int. Ed. 2015, 54, 13550.
(a) Meth-Cohn, O.; Narine, B.; Tarnowski, B. J. Chem. Soc., Perkin Trans. 1 1981, 1520. (b) Meth-Cohn, O.; Narine, B.; Tarnowski, B.; Hayes, R.; Keyzad, A.; Rhouati, S.; Robinson, A. J. Chem. Soc., Perkin Trans. 1 1981, 2509.
Danishefsky, S.; Volkmann, R. Tetrahedron Lett. 1973, 2521.
(a) Danishefsky, S.; Berman, E.; Clizbe, L. A.; Hirama, M. J. Am. Chem. Soc. 1979, 101, 4385. (b) Morera, E.; Pinnen, F.; Lucente, G. Org. Lett. 2002, 4, 1139.
Brunin, T.; Legentil, L.; Hénichart, J.-P.; Rigo, B. Tetrahedron 2006, 62, 3959.
(a) Boch, M.; Korth, T.; Nelke, J. M.; Pike, D.; Radunz, H.; Winterfeldt, E. Chem. Ber. 1972, 105, 2126. (b) Tagami, K.; Nakazawa, N.; Sano, S.; Nagao, Y. Heterocycles 2000, 53, 771. (c) Tang, C. S. F.; Morrow, C. J.; Rapoport, H. J. Am. Chem. Soc. 1975, 97, 159. (d) Brown, R. T.; Liu, J.; Santos, C. A. M. Tetrahedron Lett. 2000, 41, 859. (e) Shen, W.; Coburn, C. A.; Bornmann, W. G.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 611. (f) Davis, F. A.; Weismiller, M. C. J. Org. Chem. 1990, 55, 3715. (g) Li, K.; Ou, J.; Gao, S. Angew. Chem., Int. Ed. 2016, 55, 14778.
Evans, D. A.; Adams, D. J. J. Am. Chem. Soc. 2007, 129, 1048. (b) Bonin, M.; Royer, J.; Grierson, D. S.; Husson, H.-P. Tetrahedron Lett. 1986, 27, 1569.
(a) Blagg, B. S. J.; Boger, D. L. Tetrahedron 2002, 58, 6343. (b) Bennasar, M.-L.; Zulaica, E.; Juan, C.; Alonso, Y.; Bosch, J. J. Org. Chem. 2002, 67, 7465. (c) Brown, R. T.; Liu, J.; Santos, C. A. M. Tetrahedron Lett. 2000, 41, 859.
Wagh, M. B.; Shankar, R.; Kumar, U. K. S.; Gill, C. H. Synlett 2011, 84.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Khimiya Geterotsiklicheskikh Soedinenii 2017 53(4) 434–445
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(PDF 1782 kb)
Rights and permissions
About this article
Cite this article
Tietze, L.F., Bischoff, M., Khan, T.A. et al. Synthesis of indolizinoquinolinones through three- and four-component domino Knoevenagel / hetero-Diels–Alder reactions: novel access to (+)-camptothecin. Chem Heterocycl Comp 53, 434–445 (2017). https://doi.org/10.1007/s10593-017-2070-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-017-2070-4