Low-Valent Titanium-Mediated Enantioselective Synthesis of Quinazolinone Alkaloids Circumdatins F, H, and Analogs
Shi-Peng Luo
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Search for more papers by this authorHui Geng
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Search for more papers by this authorYu Wang
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Search for more papers by this authorCorresponding Author
Pei-Qiang Huang
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China, Tel.: 0086-0592-2182240; Fax: 0086-0592-2189959Search for more papers by this authorShi-Peng Luo
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Search for more papers by this authorHui Geng
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Search for more papers by this authorYu Wang
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Search for more papers by this authorCorresponding Author
Pei-Qiang Huang
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China
Department of Chemistry and Fujian Provincial Key Laboratory for Chemical Biology, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, Fujian 361005, China, Tel.: 0086-0592-2182240; Fax: 0086-0592-2189959Search for more papers by this authorAbstract
We report the concise and protecting-group-free enantioselective total syntheses of circumdatins F and H. In view of the extreme importance of analogs of quinazolinone alkaloids in drug research and discovery, four analogs of bioactive quinazolinobenzodiazepine alkaloids, including demethoxycircumdatin H (12) and N-demethylbenzomalvin A (13), have been synthesized. The method is based on the low-valent titanium-promoted intramolecular reductive coupling of imides with o-nitrobenzimides, which yielded quinazolino[3,2-a][1,4]benzodiazepines under mild conditions. In addition, heptacyclic dehydraasperlicin E (16) has been synthesized from asperlicin C by a NCS-mediated dehydra-cyclization reaction.
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REFERENCES
- 1a Chou, T. Q.; Jang, C. S.; Fu, F. Y.; Kao, Y. S.; Huang, K. C., Science (Chinese), 1947, 29, 49.
- 1b Koepfli, J. B.; Mead, J. F.; Brockman, J. A. Jr.. J. Am. Chem. Soc., 1947, 69, 1837.
- 1c Chou, T.-Q.; Fu, F. Y.; Kao, Y. S.. J. Am. Chem. Soc., 1948, 70, 1765.
- 1d Koepfli, J. B.; Mead, J. F.; Brockman, J. A.Jr.. J. Am. Chem. Soc., 1949, 71, 1048.
- 1e Akssira, M.; Boumzebra, M.; Kasmi, H.; Dahdouh, A.. Tetrahedron, 1994, 50, 9051.
- 1f Kamal, A.; Ramana, A. K.; Reddy, S.; Ramana, K. V.; Babu, A. H.; Prasad, B. R.. Tetrahedron Lett., 2004, 45, 8187.
- 1g Jadidi, K.; Aryan, R.; Mehrdad, M.; Lügger, T. F.; Hahnb, E.; Ng, S. W.. J. Mol. Struct., 2004, 692, 37.
- 1h Wright, W. B.; Brabander, H. J.; Greenblatt, E. N.; Day, I. P.; Hardy, R. A.. J. Med. Chem., 1978, 21, 1087.
- 1i Hoffmann, E.; Jagnicinski, B.. J. Heterocycl. Chem., 1966, 348.
- 2For recent reviews on the quinazoline alkaloids, see:
- 2a Egushi, S., Topics in Heterocyclic Chemistry, Springer-verlag, Berlin Heidelberg, 2006.
- 2b Mhaske, S. B.; Argade, N. P.. Tetrahedron, 2006, 62, 9787.
- 2c Michael, J. P.. Nat. Prod. Rep., 2008, 25, 166 and references cited therein.
- 3a Goetz, M. A.; Lopez, M.; Monaghan, R. L.; Chang, R. S. L.; Lotti, V. J.; Chen, T. B.. J. Antibiot., 1985, 38, 1633.
- 3b Liesch, J. M.; Hensens, O. D.; Springer, J. P.; Chang, R. S. L.; Lotti, V. J.. J. Antibiot., 1985, 38, 1638.
- 3c
Goetz, M. A.;
Monaghan, R. L.;
Chang, R. S. L.;
Ondeyka, J.;
Chen, T. B.;
Lotti, V. J..
J. Antibiot.,
1988,
39,
875.
10.7164/antibiotics.41.875 Google Scholar
- 3d Liesch, J. M.; Hensens, O. D.; Zink, D. L.; Goetz, M. A.. J. Antibiot., 1988, 41, 878.
- 3e Houck, D. R.; Ondeyka, J.; Zink, D. L.; Inamine, E.; Goetz, M. A.; Hensens, O. D.. J. Antibiot., 1988, 41, 882.
- 4 Sun, H. H.; Barrow, C. J.; Sedlock, D. M.; Gillum, A. M.; Cooper, R.. J. Antibiot., 1994, 47, 515.
- 5a Rahbak, L.; Breinholt, J.. J. Nat. Prod., 1999, 62, 904.
- 5b Rahbak, L.; Breinholt, J.; Frisvad, J. C.; Christophersen, C.. J. Org. Chem., 1999, 64, 1689.
- 5c Dai, J.-R.; Carte, B. K.; Sidebottom, P. J.; Yew, A. L.; Ng, S.-W.; Huang, Y.; Butler, M. S.. J. Nat. Prod., 2001, 64, 125.
- 5d López-Gresa, M. P.; González, M. C.; Primo, J.; Moya, P.; Romeroand, V.; Estornell, E.. J. Antibiot., 2005, 58, 416.
- 6For reviews, see:
- 6a Antonow, D.; Thurston, D. E.. Chem. Rev., 2011, 111, 2815.
- 6b Thurston, D. E.; Bose, D. S.. Chem. Rev., 1994, 94, 433.
- 7For the enantioselective syntheses of asperlicin C, see:
- 7a Bock, M. G.; Dipardo, R. M.; Pitzenberger, S. M.; Hominick, C. F.; Springer, J. P.; Freidinger, R. M.. J. Org. Chem., 1987, 52, 1644.
- 7b He, F.; Foxman, B. M.; Snider, B. B.. J. Am. Chem. Soc., 1998, 120, 6417.
- 7c Tseng, M. C.; Lai, C. Y.; Chu, Y. W.; Chu, Y. H.. Chem. Commun., 2009, 445.
- 7d Tseng, M. C.; Yang, H. Y.; Chu, Y. H.. Org. Biomol. Chem., 2010, 10, 419.
- 7e
Al-Said, N. H.;
Shawakfeh, K. Q.;
Ibrahim, M. I.;
Tayyem, S. H..
Arkivoc,
2010,
(ix),
282.
10.3998/ark.5550190.0011.926 Google Scholar
- 7f For a racemic synthesis, see: Liu, J. F.; Kaselj, M.; Isome, Y.; Chapnick, J.; Zhang, B. L.; Bi, G.; Yohannes, D.; Yu, L. B.; Baldino, C. M.. J. Org. Chem., 2005, 70, 10488.
- 8 For the sole total synthesis of asperlicin E, see: ref. 7a.
- 9For the enantioselective syntheses of circumdatin F, see:
- 9a Busuyek, M. V.; Snider, B. B.. Tetrahedron, 2001, 57, 3301.
- 9b Kshirsagar, U. A.; Mhaske, S. B.; Argade, N. P.. Tetrahedron Lett., 2007, 48, 3243.
- 9c ref. 7c.
- 9d ref. 7d
- 9e For racemic syntheses, see: Witt, A.; Bergman, J.. J. Org. Chem., 2001, 66, 2784.
- 9f Witt, A.; Bergman, J.. J. Heterocycl. Chem., 2002, 39, 351.
- 9g ref. 7f.
- 10For the enantioselective syntheses of circumdatin H, see:
- 10a Bose, D. S.; Chary, M. V.. Synthesis, 2010, 643.
- 10b ref. 7e.
- 10c Zhichkin, P. E.; Jin, X. M.; Zhang, H. L.; Peterson, L. H.; Ramirez, C.; Snyder, T. S.; Burton, H. S.. Org. Biomol. Chem., 2010, 10, 1287.
- 10d Kshirsagar, U. A.; Argade, N. P.. Org. Lett., 2010, 12, 3716.
- 10e Sorra, K.; Mukkanti, K.; Pusuluri, S.. Tetrahedron, 2012, 68, 2001.
- 11For the enantioselective synthesis of benzomalvin A, see:
- 11a Sugimori, T.; Okawa, T.; Eguchi, S.; Kakehi, A.; Yashimaand, E.; Okamoto, Y.. Tetrahedron, 1998, 54, 7997. For the enantioselective synthesis of demethylbenzomalvin A, see: ref. 7d. For a racemic synthesis, see: ref. 7f.
- 12For selected other syntheses, see:
- 12a Al-Said, N. H.; Al-Qaisi, L. S.. Tetrahedron Lett., 2006, 47, 693.
- 12b Grieder, A.; Thomas, A. D.. Synthesis, 2003, 1707.
- 12c Zhang, W.; Williams, J. P.; Lu, Y. M.; Nagashimaa, T.; Chu, Q. L.. Tetrahedron Lett., 2007, 48, 563.
- 12d Lu, Y.; Nagashima, T.; Miriyala, B.; Conde, J.; Zhang, W.. J. Comb. Chem., 2010, 12, 125.
- 12e Pettersson, B.; Hasimbegovic, V.; Bergman, J.. Tetrahedron Lett., 2010, 51, 238.
- 12f Pettersson, B.; Hasimbegovic, V.; Bergman, J.. J. Org. Chem., 2011, 76, 1554.
- 12g Kumaraswamy, S.; Mukkanti, K.; Srinivas, P.. Synthesis, 2014, 46, 189.
- 13a Xiao, K.-J.; Luo, J.-M.; Xia, X.-E.; Wang, Y.; Huang, P.-Q.. Chem.-Eur. J., 2013, 19, 13075.
- 13b Huang, S.-Y.; Chang, Z.; Tuo, S.-C.; Gao, L.-H.; Wang, A.-E; Huang, P.-Q.. Chem. Commun., 2013, 49, 7088.
- 14a Xiao, K.-J.; Wang, A.-E; Huang, Y.-H.; Huang, P.-Q.. Asian J. Org. Chem., 2012, 1, 130.
- 14b Xiao, K.-J.; Huang, Y.-H.; Huang, P.-Q.. Acta Chim. Sinica, 2012, 70, 1917.
- 14c Xiao, K.-J.; Wang, A.-E; Huang, P.-Q.. Angew. Chem., Int. Ed., 2012, 51, 8314.
- 14d Xiao, K.-J.; Luo, J.-M.; Ye, K.-Y.; Wang, Y.; Huang, P.-Q.. Angew. Chem., Int. Ed., 2010, 49, 3037.
- 15a Huang, P.-Q.; Liu, L.-X.; Peng, Q.-L.. ZL 200910110953.2 Chem. Abstr., CN 20091110953, 2009, 20090122.
- 15b Peng, Q.-L.; Luo, S.-P.; Xia, X.-E.; Liu, L.-X.; Huang, P.-Q.. Chem. Commun., 2014, 50, 1986.
- 15c Xu, C.-P.; Luo, S.-P.; Wang, A.-E; Huang, P.-Q.. Org. Biomol. Chem., 2014, 12, 2859.
- 15d Luo, S.-P.; Peng, Q.-L.; Xu, C.-P.; Wang, A.-E; Huang, P.-Q.. Chinese J. Chem., 2014, 32, 757.
- 16 Huang, P.-Q.; Wang, Y.; Luo, S.-P.; Geng, H.; Ruan, Y.-P.; Wang, A.-E. Tetrahedron Lett., 2015, 56, 1255.
- 17a Gates, M.. J. Org. Chem., 1980, 45, 1675.
- 17b Bhat, B.; Harrison, D. M.. Tetrahedron, 1993, 49, 10655.
- 17c Clark, R. L.; Carter, K. C.; Mullen, A. B.; Geoffrey, D.; Coxon, G. D.; Owusu-Dapaah, G.; McFarlane, E.; Thi, M. D. D.; Grant, M. H.; Tettey, J. N. A.; Mackay, S. P.. Bioorg. Med. Chem. Lett., 2007, 17, 624.
- 18For recent reviews on the synthesis of quinazolinones and quinazolines, see:
- 18a Imtiaz, K.; Aliya, I.; Naeem, A.; Aamer, S.. Eur. J. Med. Chem., 2014, 76, 193.
- 18b Connolly, D. J.; Cusack, D.; O'Sullivan, T. P.; Guiry, P. J.. Tetrahedron, 2005, 61, 10153.
- 18c For selected recent methods, see: Zhao, D.; Wang, T.; Li, J.-X.. Chem. Commun., 2014, 50, 6471.
- 18d Jiang, X.; Tang, T.; Wang, J.-M.; Chen, Z.; Zhu, Y.-M.; Ji, S.-J.. J. Org. Chem., 2014, 79, 5082.
- 18e Wang, L.-X.; Xiang, J.-F.; Tang, Y.-L.. Eur. J. Org. Chem., 2014, 2682.
- 18f Ramamohan, M.; Raghunadh, A.; Rao, K. R.; Kothapalli, B. C.; Sridhar, R.; Jayaprakash, S.. Synlett, 2014, 25, 821.
- 18g Wu, X.-F.; He, L.; Neumann, H.; Beller, M.. Chem.-Eur. J., 2013, 19, 12635.
- 18h Zhu, Y.-P.; Fei, Z.; Liu, M.-C.; Jia, F.-C.; Wu, A.-X.. Org. Lett., 2013, 15, 378.
- 18i Cheng, R.; Guo, T.; Zhang-Negrerie, D.; Du, Y.; Zhao, K.. Synthesis, 2013, 45, 2998.
- 18j Xu, L.; Jiang, Y.; Ma, D.. Org. Lett., 2012, 14, 1150.
- 18k Xu, W.; Jin, Y.; Liu, H.; Jiang, Y.; Fu, H.. Org. Lett., 2011, 13, 1274.
- 18l Xu, W.; Fu, H.. J. Org. Chem., 2011, 76, 3846.
- 18m Liu, X.; Fu, H.; Jiang, Y.; Zhao, Y.. Angew. Chem., Int. Ed., 2009, 48, 348.
- 18n Shankaraiah, N.; Markandeya, N.; Espinoza-Moraga, M.; Arancibia, C.; Kamal, A.; Santos, L. S.. Synthesis, 2009, 13, 2163.
- 19a Takeuchi, H.; Hagiwara, S.; Eguchi, S.. Tetrahedron, 1989, 45, 6375.
- 19b Marsden, S. P.; Depew, K. M.; Danishefsky, S. J.. J. Am. Chem. Soc., 1994, 116, 11143.
- 20a Akazome, M.; Kondo, T.; Watanabe, Y.. J. Org. Chem., 1993, 58, 310.
- 20b Zhichkin, P.; Kesicki, E.; Treiberg, J.; Bourdon, L.; Ronsheim, M.; Ooi, H. C.; White, S.; Judkins, A.; Fairfax, D.. Org. Lett., 2007, 9, 1415.
- 21 Asahina, Y.; Ohta, T.. Yakugaku Zasshi, 1928, 48, 313.
- 22 Levy, P. B.; Stephen, H.. J. Chem. Soc., 1956, 985.
- 23a Mumm, O.; Hesse, H.. Chem. Ber., 1910, 43, 2505.
- 23b
Spath, E.;
Platzer, N..
Chem. Ber.,
1935,
68,
2221.
10.1002/cber.19350681212 Google Scholar
- 24a McMurry, J. E.. Acc. Chem. Res., 1974, 7, 281.
- 24b Wong, H. N. C.. Acc. Chem. Res., 1989, 22, 145.
- 24c McMurry, J. E.. Chem. Rev., 1989, 89, 1513.
- 24d For recent examples, see: Lin, W.; Hu, M. H.; Feng, X.; Fu, L.; Cao, C. P.; Huang, Z. B.; Shi, D. Q.. Tetrahedron Lett., 2014, 55, 2238.
- 24e Lin, W.; Hu, M. H.; Feng, X.; Fu, L.; Cao, C. P.; Huang, Z. B.; Shi, D. Q.. Tetrahedron, 2013, 69, 6721.
- 24f Sun, F.; Feng, X.; Zhao, X.; Huang, Z. B.; Shi, D. Q.. Tetrahedron, 2012, 68, 3851.
- 24g Sun, F.; Feng, X.; Zhao, X.; Shi, D. Q.. Tetrahedron Lett., 2011, 52, 5633.
- 24h Zhong, W. H.; Zhang, Y. M.; Chen, X. Y.. Tetrahedron Lett., 2001, 42, 73.
- 25a Shi, D. Q.; Rong, L. C.; Wang, J. X.; Zhuang, Q. Y.; Wang, X. S.; Hu, H. W.. Tetrahedron Lett., 2004, 45, 3199.
- 25b Shi, D. Q.; Wang, X. S.; Tu, S. J.; Hu, H. W.. Chinese J. Struct. Chem., 2003, 22, 581.
- 25c Shi, D. Q.; Wang, J. X.; Rong, L. C.; Zhuang, Q. Y.; Hu, H. W.. Chem. J. Chin. Univ., 2004, 25, 462.
- 26 Blass, B. E.; Burt, T. M.; Liu, S.; Portlock, D. E.; Swing, E. M.. Tetrahedron Lett., 2000, 41, 2063.
- 27 Due to the scarcity of the natural product originally isolated (0.6 mg), the physical properties of the natural circumdatin F were not reported (ref. 5a). In the second reported isolation from natural source, 2 mg of circumdatin F was obtained as a white powder with [α]D (−18.9 (c 0.11, MeOH), Ref. 5c.
- 28a Alexis, C.; Ganesan, K.; François, C.; Gwilherm, E.. Synthesis, 2009, 17, 2927.
- 28b Malgesini, B.; Forte, B.; Borghi, D.; Quartieri, F.; Gennari, C.; Papeo, G.. Chem. Eur. J., 2009, 15, 7922.
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