Low-valent titanium-mediated enantioselective synthesis of quinazolinone alkaloids circumdatins F, H, and analogs

Chinese Journal of Chemistry

Volumn 33, Issue 6, 2015, Pages 646-654

  Luo, Shi Peng ^a   Geng, Hui ^a   Wang, Yu ^a   Huang, Pei Qiang ^a  

^a XIAMEN UNIVERSITY   (China)

Author keywords

low valent titanium; natural products; protecting group free; synthetic methods; total synthesis

Indexed keywords

EID: 85027944910     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201400849     Document Type: Article

References (96)

1. Chou, T. Q.,;, Jang, C. S.,;, Fu, F. Y.,;, Kao, Y. S.,;, Huang, K. C., Science (Chinese), 1947, 29, 49.
2. Koepfli, J. B.,;, Mead, J. F.,;, Brockman, J. A. Jr.,. J. Am. Chem. Soc., 1947, 69, 1837.
3. Chou, T.-Q.,;, Fu, F. Y.,;, Kao, Y. S.,. J. Am. Chem. Soc., 1948, 70, 1765.
4. Koepfli, J. B.,;, Mead, J. F.,;, Brockman, J. A. Jr.,. J. Am. Chem. Soc., 1949, 71, 1048.
5. Akssira, M.,;, Boumzebra, M.,;, Kasmi, H.,;, Dahdouh, A.,. Tetrahedron, 1994, 50, 9051.
6. Kamal, A.,;, Ramana, A. K.,;, Reddy, S.,;, Ramana, K. V.,;, Babu, A. H.,;, Prasad, B. R.,. Tetrahedron Lett., 2004, 45, 8187.
7. Jadidi, K.,;, Aryan, R.,;, Mehrdad, M.,;, Lügger, T. F.,;, Hahnb, E.,;, Ng, S. W.,. J. Mol. Struct., 2004, 692, 37.
8. Wright, W. B.,;, Brabander, H. J.,;, Greenblatt, E. N.,;, Day, I. P.,;, Hardy, R. A.,. J. Med. Chem., 1978, 21, 1087.
9. Hoffmann, E.,;, Jagnicinski, B.,. J. Heterocycl. Chem., 1966, 348.
10. Egushi, S., Topics in Heterocyclic Chemistry, Springer-verlag, Berlin Heidelberg, 2006.
11. Mhaske, S. B.,;, Argade, N. P.,. Tetrahedron, 2006, 62, 9787.
12. Michael, J. P.,. Nat. Prod. Rep., 2008, 25, 166 and references cited therein.
13. Goetz, M. A.,;, Lopez, M.,;, Monaghan, R. L.,;, Chang, R. S. L.,;, Lotti, V. J.,;, Chen, T. B.,. J. Antibiot., 1985, 38, 1633.
14. Liesch, J. M.,;, Hensens, O. D.,;, Springer, J. P.,;, Chang, R. S. L.,;, Lotti, V. J.,. J. Antibiot., 1985, 38, 1638.
15. Goetz, M. A.,;, Monaghan, R. L.,;, Chang, R. S. L.,;, Ondeyka, J.,;, Chen, T. B.,;, Lotti, V. J.,. J. Antibiot., 1988, 39, 875.
16. Liesch, J. M.,;, Hensens, O. D.,;, Zink, D. L.,;, Goetz, M. A.,. J. Antibiot., 1988, 41, 878.
17. Houck, D. R.,;, Ondeyka, J.,;, Zink, D. L.,;, Inamine, E.,;, Goetz, M. A.,;, Hensens, O. D.,. J. Antibiot., 1988, 41, 882.
18. Sun, H. H.,;, Barrow, C. J.,;, Sedlock, D. M.,;, Gillum, A. M.,;, Cooper, R.,. J. Antibiot., 1994, 47, 515.
19. Rahbak, L.,;, Breinholt, J.,. J. Nat. Prod., 1999, 62, 904.
20. Rahbak, L.,;, Breinholt, J.,;, Frisvad, J. C.,;, Christophersen, C.,. J. Org. Chem., 1999, 64, 1689.
21. 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.
22. Lõpez-Gresa, M. P.,;, González, M. C.,;, Primo, J.,;, Moya, P.,;, Romeroand, V.,;, Estornell, E.,. J. Antibiot., 2005, 58, 416.
23. Antonow, D.,;, Thurston, D. E.,. Chem. Rev., 2011, 111, 2815.
24. Thurston, D. E.,;, Bose, D. S.,. Chem. Rev., 1994, 94, 433.
25. Bock, M. G.,;, Dipardo, R. M.,;, Pitzenberger, S. M.,;, Hominick, C. F.,;, Springer, J. P.,;, Freidinger, R. M.,. J. Org. Chem., 1987, 52, 1644.
26. He, F.,;, Foxman, B. M.,;, Snider, B. B.,. J. Am. Chem. Soc., 1998, 120, 6417.
27. Tseng, M. C.,;, Lai, C. Y.,;, Chu, Y. W.,;, Chu, Y. H.,. Chem. Commun., 2009, 445.
28. Tseng, M. C.,;, Yang, H. Y.,;, Chu, Y. H.,. Org. Biomol. Chem., 2010, 10, 419.
29. Al-Said, N. H.,;, Shawakfeh, K. Q.,;, Ibrahim, M. I.,;, Tayyem, S. H.,. Arkivoc, 2010, (ix), 282.
30. 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.
31. Busuyek, M. V.,;, Snider, B. B.,. Tetrahedron, 2001, 57, 3301.
32. Kshirsagar, U. A.,;, Mhaske, S. B.,;, Argade, N. P.,. Tetrahedron Lett., 2007, 48, 3243.
33. For racemic syntheses, see:, Witt, A.,;, Bergman, J.,. J. Org. Chem., 2001, 66, 2784.
34. Witt, A.,;, Bergman, J.,. J. Heterocycl. Chem., 2002, 39, 351.
35. Bose, D. S.,;, Chary, M. V.,. Synthesis, 2010, 643.
36. 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.
37. Kshirsagar, U. A.,;, Argade, N. P.,. Org. Lett., 2010, 12, 3716.
38. Sorra, K.,;, Mukkanti, K.,;, Pusuluri, S.,. Tetrahedron, 2012, 68, 2001.
39. 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.
40. Al-Said, N. H.,;, Al-Qaisi, L. S.,. Tetrahedron Lett., 2006, 47, 693.
41. Grieder, A.,;, Thomas, A. D.,. Synthesis, 2003, 1707.
42. Zhang, W.,;, Williams, J. P.,;, Lu, Y. M.,;, Nagashimaa, T.,;, Chu, Q. L.,. Tetrahedron Lett., 2007, 48, 563.
43. Lu, Y.,;, Nagashima, T.,;, Miriyala, B.,;, Conde, J.,;, Zhang, W.,. J. Comb. Chem., 2010, 12, 125.
44. Pettersson, B.,;, Hasimbegovic, V.,;, Bergman, J.,. Tetrahedron Lett., 2010, 51, 238.
45. Pettersson, B.,;, Hasimbegovic, V.,;, Bergman, J.,. J. Org. Chem., 2011, 76, 1554.
46. Kumaraswamy, S.,;, Mukkanti, K.,;, Srinivas, P.,. Synthesis, 2014, 46, 189.
47. Xiao, K.-J.,;, Luo, J.-M.,;, Xia, X.-E.,;, Wang, Y.,;, Huang, P.-Q.,. Chem.-Eur. J., 2013, 19, 13075.
48. Huang, S.-Y.,;, Chang, Z.,;, Tuo, S.-C.,;, Gao, L.-H.,;, Wang, A.-E,;, Huang, P.-Q.,. Chem. Commun., 2013, 49, 7088.
49. Xiao, K.-J.,;, Wang, A.-E,;, Huang, Y.-H.,;, Huang, P.-Q.,. Asian J. Org. Chem., 2012, 1, 130.
50. Xiao, K.-J.,;, Huang, Y.-H.,;, Huang, P.-Q.,. Acta Chim. Sinica, 2012, 70, 1917.
51. Xiao, K.-J.,;, Wang, A.-E,;, Huang, P.-Q.,. Angew. Chem., Int. Ed., 2012, 51, 8314.
52. Xiao, K.-J.,;, Luo, J.-M.,;, Ye, K.-Y.,;, Wang, Y.,;, Huang, P.-Q.,. Angew. Chem., Int. Ed., 2010, 49, 3037.
53. Huang, P.-Q.,;, Liu, L.-X.,;, Peng, Q.-L.,. ZL 200910110953.2 Chem. Abstr., CN 20091110953, 2009, 20090122.
54. Peng, Q.-L.,;, Luo, S.-P.,;, Xia, X.-E.,;, Liu, L.-X.,;, Huang, P.-Q.,. Chem. Commun., 2014, 50, 1986.
55. Xu, C.-P.,;, Luo, S.-P.,;, Wang, A.-E,;, Huang, P.-Q.,. Org. Biomol. Chem., 2014, 12, 2859.
56. Luo, S.-P.,;, Peng, Q.-L.,;, Xu, C.-P.,;, Wang, A.-E,;, Huang, P.-Q.,. Chinese J. Chem., 2014, 32, 757.
57. Huang, P.-Q.,;, Wang, Y.,;, Luo, S.-P.,;, Geng, H.,;, Ruan, Y.-P.,;, Wang, A.-E,. Tetrahedron Lett., 2015, 56, 1255.
58. Gates, M.,. J. Org. Chem., 1980, 45, 1675.
59. Bhat, B.,;, Harrison, D. M.,. Tetrahedron, 1993, 49, 10655.
60. 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.
61. Imtiaz, K.,;, Aliya, I.,;, Naeem, A.,;, Aamer, S.,. Eur. J. Med. Chem., 2014, 76, 193.
62. Connolly, D. J.,;, Cusack, D.,;, O'Sullivan, T. P.,;, Guiry, P. J.,. Tetrahedron, 2005, 61, 10153.
63. For selected recent methods, see:, Zhao, D.,;, Wang, T.,;, Li, J.-X.,. Chem. Commun., 2014, 50, 6471.
64. Jiang, X.,;, Tang, T.,;, Wang, J.-M.,;, Chen, Z.,;, Zhu, Y.-M.,;, Ji, S.-J.,. J. Org. Chem., 2014, 79, 5082.
65. Wang, L.-X.,;, Xiang, J.-F.,;, Tang, Y.-L.,. Eur. J. Org. Chem., 2014, 2682.
66. Ramamohan, M.,;, Raghunadh, A.,;, Rao, K. R.,;, Kothapalli, B. C.,;, Sridhar, R.,;, Jayaprakash, S.,. Synlett, 2014, 25, 821.
67. Wu, X.-F.,;, He, L.,;, Neumann, H.,;, Beller, M.,. Chem.-Eur. J., 2013, 19, 12635.
68. Zhu, Y.-P.,;, Fei, Z.,;, Liu, M.-C.,;, Jia, F.-C.,;, Wu, A.-X.,. Org. Lett., 2013, 15, 378.
69. Cheng, R.,;, Guo, T.,;, Zhang-Negrerie, D.,;, Du, Y.,;, Zhao, K.,. Synthesis, 2013, 45, 2998.
70. Xu, L.,;, Jiang, Y.,;, Ma, D.,. Org. Lett., 2012, 14, 1150.
71. Xu, W.,;, Jin, Y.,;, Liu, H.,;, Jiang, Y.,;, Fu, H.,. Org. Lett., 2011, 13, 1274.
72. Xu, W.,;, Fu, H.,. J. Org. Chem., 2011, 76, 3846.
73. Liu, X.,;, Fu, H.,;, Jiang, Y.,;, Zhao, Y.,. Angew. Chem., Int. Ed., 2009, 48, 348.
74. Shankaraiah, N.,;, Markandeya, N.,;, Espinoza-Moraga, M.,;, Arancibia, C.,;, Kamal, A.,;, Santos, L. S.,. Synthesis, 2009, 13, 2163.
75. Takeuchi, H.,;, Hagiwara, S.,;, Eguchi, S.,. Tetrahedron, 1989, 45, 6375.
76. Marsden, S. P.,;, Depew, K. M.,;, Danishefsky, S. J.,. J. Am. Chem. Soc., 1994, 116, 11143.
77. Akazome, M.,;, Kondo, T.,;, Watanabe, Y.,. J. Org. Chem., 1993, 58, 310.
78. Zhichkin, P.,;, Kesicki, E.,;, Treiberg, J.,;, Bourdon, L.,;, Ronsheim, M.,;, Ooi, H. C.,;, White, S.,;, Judkins, A.,;, Fairfax, D.,. Org. Lett., 2007, 9, 1415.
79. Asahina, Y.,;, Ohta, T.,. Yakugaku Zasshi, 1928, 48, 313.
80. Levy, P. B.,;, Stephen, H.,. J. Chem. Soc., 1956, 985.
81. Mumm, O.,;, Hesse, H.,. Chem. Ber., 1910, 43, 2505.
82. Spath, E.,;, Platzer, N.,. Chem. Ber., 1935, 68, 2221.
83. McMurry, J. E.,. Acc. Chem. Res., 1974, 7, 281.
84. Wong, H. N. C.,. Acc. Chem. Res., 1989, 22, 145.
85. McMurry, J. E.,. Chem. Rev., 1989, 89, 1513.
86. 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.
87. Lin, W.,;, Hu, M. H.,;, Feng, X.,;, Fu, L.,;, Cao, C. P.,;, Huang, Z. B.,;, Shi, D. Q.,. Tetrahedron, 2013, 69, 6721.
88. Sun, F.,;, Feng, X.,;, Zhao, X.,;, Huang, Z. B.,;, Shi, D. Q.,. Tetrahedron, 2012, 68, 3851.
89. Sun, F.,;, Feng, X.,;, Zhao, X.,;, Shi, D. Q.,. Tetrahedron Lett., 2011, 52, 5633.
90. Zhong, W. H.,;, Zhang, Y. M.,;, Chen, X. Y.,. Tetrahedron Lett., 2001, 42, 73.
91. Shi, D. Q.,;, Rong, L. C.,;, Wang, J. X.,;, Zhuang, Q. Y.,;, Wang, X. S.,;, Hu, H. W.,. Tetrahedron Lett., 2004, 45, 3199.
92. Shi, D. Q.,;, Wang, X. S.,;, Tu, S. J.,;, Hu, H. W.,. Chinese J. Struct. Chem., 2003, 22, 581.
93. Shi, D. Q.,;, Wang, J. X.,;, Rong, L. C.,;, Zhuang, Q. Y.,;, Hu, H. W.,. Chem. J. Chin. Univ., 2004, 25, 462.
94. Blass, B. E.,;, Burt, T. M.,;, Liu, S.,;, Portlock, D. E.,;, Swing, E. M.,. Tetrahedron Lett., 2000, 41, 2063.
95. Alexis, C.,;, Ganesan, K.,;, François, C.,;, Gwilherm, E.,. Synthesis, 2009, 17, 2927.
96. Malgesini, B.,;, Forte, B.,;, Borghi, D.,;, Quartieri, F.,;, Gennari, C.,;, Papeo, G.,. Chem. Eur. J., 2009, 15, 7922.