Total synthesis of viridicatumtoxin B and analogues thereof: Strategy evolution, structural revision, and biological evaluation

Journal of the American Chemical Society

Volumn 136, Issue 34, 2014, Pages 12137-12160

  Nicolaou, K C ^a,b   Hale, Christopher R H ^a,b   Nilewski, Christian ^a,b   Ioannidou, Heraklidia A ^a,b   Elmarrouni, Abdelatif ^a,b   Nilewski, Lizanne G ^a,b   Beabout, Kathryn ^a   Wang, Tim T ^a   Shamoo, Yousif ^a  

^a RICE UNIVERSITY   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGY;

BACTERIAL STRAINS; BIOLOGICAL EVALUATION; DIECKMANN REACTION; DRUG-RESISTANT PATHOGENS; REACTIVITY PATTERN; STRUCTURE ACTIVITY RELATIONSHIPS; SYNTHETIC STRATEGIES; TETRACYCLINE ANTIBIOTICS;

SYNTHESIS (CHEMICAL);

ANTIBIOTIC AGENT; CARBON; HYDROXYL GROUP; LEWIS ACID; UNCLASSIFIED DRUG; VIRIDICATUMTOXIN B; ANTIINFECTIVE AGENT; TETRACYCLINE DERIVATIVE; TETRACYCLINE; TOXIN;

ALKYLATION; AROMATIZATION; ARTICLE; BACTERIAL STRAIN; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; EVOLUTION; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; OXIDATION; PATHOGENESIS; STRUCTURE ACTIVITY RELATION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; MICROBIAL SENSITIVITY TEST; SYNTHESIS; ANTIBACTERIAL ACTIVITY; DIECKMANN REACTION; HYDROXYLATION; NONHUMAN;

ALKYLATION; ANTI-BACTERIAL AGENTS; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; LEWIS ACIDS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; TETRACYCLINES;

EID: 84906728546     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja506472u     Document Type: Article

References (137)

1. Zheng, C. J.; Yu, H. E.; Kim, E. H.; Kim, W. G. J. Antibiot. 2008, 61, 633-637
2. Hutchison, R. D.; Steyn, P. S.; van Rensberg, S. J. Toxicol. Appl. Pharmacol. 1973, 24, 507-509
3. Inokoshi, J.; Nakamura, Y.; Hongbin, Z.; Uchida, R.; Nonaka, K.; Masuma, R.; Tomoda, H. J. Antibiot. 2013, 66, 37-41
4. Duggar, B. M. Ann. N.Y. Acad. Sci. 1948, 51, 177-181
5. Dougherty, T. J.; Pucci, M. J. Antibiotic Discovery and Development; Springer: New York, 2012.
6. Tally, F. T.; Ellestad, G. A.; Testa, R. T. J. Antimicrob. Chemother. 1995, 35, 449-452
7. Sutcliffe, J. A.; O'Brien, W.; Fyfe, C.; Grossman, T. H. Antimicrob. Agents Chemother. 2013, 57, 5548-5558
8. Chopra, I.; Roberts, M. Microbiol. Mol. Biol. R. 2001, 65, 232-260
9. Breinholt, J.; Jensen, G. W.; Kjaer, A.; Olsen, C. E.; Rosendahl, C. N. Acta Chem. Scand. 1997, 51, 855-860
10. Wong, S. M.; Kullnig, R.; Dedinas, J.; Appell, K. C.; Kydd, G. C.; Gillum, A. M.; Cooper, R.; Moore, R. J. Antibiot. 1993, 46, 214-221
11. Ishimaru, T.; Tsuboya, S.; Saijo, T. (Takeda Chem. Ind. Ltd.). JP Patent 06,40995A, March 17, 1993.
12. Kodukula, K.; Arcuri, M.; Cutrone, J. Q.; Hugill, R. M.; Lowe, S. E.; Pirnik, D. M.; Shu, Y. Z.; Fernandes, P. B.; Seethala, R. J. Antibiot. 1995, 48, 1055-1059
13. Shu, Y. Z.; Cutrone, J. F. Q.; Klohr, S. E.; Huang, S. J. Antibiot. 1995, 48, 1060-1065
14. Conover, L. H.; Korst, J. J.; Butler, K.; Woodward, R. B.; Johnston, J. D. J. Am. Chem. Soc. 1962, 84, 3222-3224
15. Korst, J. J.; Johnston, J. D.; Butler, K.; Bianco, E. J.; Conover, L. H.; Woodward, R. B. J. Am. Chem. Soc. 1968, 90, 439-457
16. Gurevich, A. I.; Karapetyan, M. G.; Kolosov, M. N.; Korobko, V. G.; Onoprienko, V. V.; Popravko, S. A.; Shemyakin, M. M. Tetrahedron Lett. 1967, 131-134
17. Muxfeldt, H.; Hardtman, G.; Kathawal, F.; Vedejs, E.; Mooberry, J. B. J. Am. Chem. Soc. 1968, 90, 6534-6536
18. Muxfeldt, H.; Haas, G.; Hardtmann, G.; Kathawala, F.; Mooberry, J. B.; Vedejs, E. J. Am. Chem. Soc. 1979, 101, 689-701
19. Barton, D. H. R. Pure Appl. Chem. 1971, 25, 5-23
20. Barton, D. H. R.; Magnus, P. D. J. Chem. Soc. C 1971, 2164-2166
21. Wasserman, H. H.; Lu, T. J.; Scott, A. I. J. Am. Chem. Soc. 1986, 108, 4237-4238
22. Stork, G.; Hagedorn, A. A. J. Am. Chem. Soc. 1978, 100, 3609-3611
23. Stork, G.; Yee, Y. K. Can. J. Chem. 1984, 62, 2627-2628
24. Stork, G.; LaClair, J. J.; Spargo, P.; Nargund, R. P.; Totah, N. J. Am. Chem. Soc. 1996, 118, 5304-5305
25. Tatsuta, K.; Yoshimoto, T.; Gunji, H.; Okado, Y.; Takahashi, M. Chem. Lett. 2000, 646-647
26. Charest, M. G.; Siegel, D. R.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 8292-8293
27. Charest, M. G.; Lerner, C. D.; Brubaker, J. D.; Siegel, D. R.; Myers, A. G. Science 2005, 308, 395-398
28. Brubaker, J. D.; Myers, A. G. Org. Lett. 2007, 9, 3523-3525
29. Sun, C. X.; Wang, Q.; Brubaker, J. D.; Wright, P. M.; Lerner, C. D.; Noson, K.; Charest, M. G.; Siegel, D. R.; Wang, Y. M.; Myers, A. G. J. Am. Chem. Soc. 2008, 130, 17913-17927
30. Kummer, D. A.; Li, D. R.; Dion, A.; Myers, A. G. Chem. Sci. 2011, 2, 1710-1718
31. Wright, P. M.; Myers, A. G. Tetrahedron 2011, 67, 9853-9869
32. Wzorek, J. S.; Knopfel, T. F.; Sapountzis, I.; Evans, D. A. Org. Lett. 2012, 14, 5840-5843
33. Kabuto, C.; Silverton, J. V.; Akiyama, T.; Sankawa, U.; Hutchison, R. D.; Steyn, P. S.; Vleggaar, R. J. Chem. Soc., Chem. Commun. 1976, 728-729
34. Silverton, J. V.; Kabuto, C.; Akiyama, T. Acta Crystallogr., Sect. B: Struct. Crystallogr. Cryst. Chem. 1982, 38, 3032-3037
35. De Jesus, A. E.; Hull, W. E.; Steyn, P. S.; Van Heerden, F. R.; Vleggaar, R. J. Chem. Soc., Chem. Commun. 1982, 902-904
36. Horak, R. M.; Maharaj, V. J.; Marais, S. F.; Van Heerden, F. R.; Vleggaar, R. J. Chem. Soc., Chem. Commun. 1988, 1562-1564
37. Chooi, Y. H.; Cacho, R.; Tang, Y. Chem. Biol. 2010, 17, 483-494
38. Chooi, Y. H.; Wang, P.; Fang, J. X.; Li, Y.; Wu, K.; Wang, P.; Tang, Y. J. Am. Chem. Soc. 2012, 134, 9428-9437
39. Chooi, Y. H.; Hong, Y. J.; Cacho, R. A.; Tantillo, D. J.; Tang, Y. J. Am. Chem. Soc. 2013, 135, 16805-16808
40. Koyama, N.; Inokoshi, J.; Tomoda, H. Molecules 2013, 18, 204-224
41. Nicolaou, K. C.; Nilewski, C.; Hale, C. R. H.; Ioannidou, H. A.; ElMarrouni, A.; Koch, L. G. Angew. Chem., Int. Ed. 2013, 52, 8736-8741
42. Dufraisse, C.; Rigaudy, J.; Basselier, J.-J.; Cuong, N. K. C. R. Acad. Sci. 1965, 260, 5031-5036
43. Rigaudy, J. Pure Appl. Chem. 1968, 16, 169-186
44. Rigaudy, J.; Deletang, C.; Basselier, J.-J. C. R. Acad. Sci. Paris 1969, 268, 344-347
45. Rigaudy, J.; Sparfel, D. Bull. Chem. Soc. Fr. 1972, 3441-3446
46. Rigaudy, J.; Sparfel, D. Tetrahedron 1978, 34, 113-121
47. Sparfel, D.; Gobert, F.; Rigaudy, J. Tetrahedron 1980, 36, 2225-2235
48. Santamaria, J.; Rigaudy, J. Tetrahedron 1980, 36, 2453-2457
49. Rigaudy, J.; Scribe, P.; Brelière, C. Tetrahedron 1981, 37, 2585-2593
50. Rigaudy, J.; Caspar, A.; Lachgar, M.; Maurette, D.; Chassagnard, C. Bull. Chem. Soc. Fr. 1992, 129, 16-24
51. Rigaudy, J.; Lachgar, M.; Saad, M. M. A. Bull. Chem. Soc. Fr. 1994, 131, 177-187
52. Rigaudy, J.; Lachgar, M.; Caspar, A.; Chassagnard, C. Bull. Chem. Soc. Fr. 1996, 133, 481-490
53. Rigaudy, J.; Lachgar, M. Tetrahedron Lett. 1997, 38, 2267-2270
54. For cobalt-mediated endoperoxide rearrangements, see: Boyd, J. D.; Foote, C. S.; Imagawa, D. K. J. Am. Chem. Soc. 1980, 102, 3641-3642
55. Other iron species are capable of inducing these rearrangements, see: Kamata, M.; Satoh, C.; Kim, H.-S.; Wataya, Y. Tetrahedron Lett. 2002, 43, 8313-8317
56. Waldemar, A.; Balci, M. Tetrahedron 1980, 36, 833-858
57. Balci, M. Chem. Rev. 1981, 81, 90-108
58. Kadás, I.; árvai, G.; Horváth, G. Org. Prep. Proced. 1998, 30, 79-85
59. Tietze, L. F.; Singidi, R. R.; Gericke, K. M. Chem.-Eur. J. 2007, 13, 9939-9947
60. Savard, J.; Brassard, P. Tetrahedron 1984, 40, 3455-3464
61. For selected examples, see ref 34 and Grunwell, J. R.; Karipides, A.; Wigal, C. T.; Heinzman, S. W.; Parlow, J.; Surso, J. A.; Clayton, L.; Fleitz, F. J.; Daffner, M.; Stevens, J. E. J. Org. Chem. 1991, 56, 91-95
62. Cameron, D. W.; Raverty, W. D. Aust. J. Chem. 1976, 29, 1523-1533
63. Schaltegger, A.; Steiger, W. Arch. Pharm. 1986, 319, 575-576
64. Müller, K.; Gürster, D.; Piwek, S.; Wiegrebe, W. J. Med. Chem. 1993, 36, 4099-4107
65. Thoma, K.; Holzmann, C. Eur. J. Pharm. Biopharm. 1998, 46, 201-208
66. Stoll, A.; Becker, B.; Helfenstein, A. Helv. Chem. Acta. 1950, 33, 313-316
67. Geiger, K. Chem. Ber. 1974, 107, 2976-2984
68. Müller, K.; Eibler, E.; Mayer, K. K.; Wiegrebe, W.; Klug, G. Arch. Pharm. 1986, 319, 2-9
69. Yamaguchi, M.; Hasebe, K.; Uchida, M.; Higashi, H.; Minami, T. Bull. Chem. Soc. Jpn. 1989, 62, 2745-2747
70. Kuhnert, N.; Molod, H. Y. Tetrahedron Lett. 2005, 46, 7571-7573
71. Davis, B. R.; Hinds, M. G.; Johnson, S. J. Aust. J. Chem. 1985, 38, 1815-1825
72. Namba, K.; Yamamoto, H.; Sasaki, I.; Mori, K.; Imagawa, H.; Mugio, N. Org. Lett. 2008, 10, 1767-1770
73. Yadav, J. S.; Thirupathaiah, B.; Al Khazim AlGhamdi, A. Eur. J. Org. Chem. 2012, 2072-2076
74. Wang, J.; Zhang, L.; Jing, Y.; Huang, W.; Zhou, X. Tetrahedron Lett. 2009, 50, 4978-4982
75. Pittman, C. U., Jr.; Miller, W. G. J. Am. Chem. Soc. 1973, 95, 2947-2956
76. Miller, W. G.; Pittman, C. U., Jr. J. Org. Chem. 1974, 39, 1955-1956
77. Gassman, P. G.; Ray, J. A.; Wenthold, P. G.; Mickelson, J. W. J. Org. Chem. 1991, 56, 5143-5146
78. Ma, S.; Zhang, J. Tetrahedron 2003, 59, 6273-6282
79. Werle, S.; Fey, T.; Neudörfl, J. M.; Schmalz, H.-G. Org. Lett. 2007, 9, 3555-3558
80. Liu, H.; Wang, Y.-H.; Zhu, L.-L.; Li, X.-X.; Zhou, W.; Chen, Z.; Hu, W.-X. Tetrahedron Lett. 2011, 52, 2990-2993
81. Moriarty, R. M.; Prakash, O. Org. React. 2004, 327-415
82. Meyer, K. H. Justus Liebigs Ann. Chem. 1911, 379, 37-78
83. Thomson, R. H. Q. Rev. Chem. Soc. 1956, 10, 27-43
84. Kündig, E. P.; Enríquez García, A.; Lomberget, T.; Bernardinelli, G. Angew. Chem., Int. Ed. 2006, 45, 98-101
85. Reviriego, F.; Alkorta, I.; Elguero, J. J. Mol. Struct. 2008, 891, 325-328
86. Bauta, W. E.; Lovett, D. P.; Cantrell, W. R., Jr.; Burke, B. D. J. Org. Chem. 2003, 68, 5967-5973
87. Pelter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677-680
88. Rathke, M. W.; Cowan, P. J. J. Org. Chem. 1985, 50, 2622-2624
89. Kornblum, N.; Smiley, R. A.; Blackwood, R. K.; Iffland, D. C. J. Am. Chem. Soc. 1955, 77, 6269-6280
90. Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378-1382
91. Tamura, Y.; Wada, A.; Kita, Y. Tetrahedron Lett. 1981, 22, 4283-4286
92. González-López, M.; Shaw, J. T. Chem. Rev. 2009, 109, 164-189
93. Ohta, Y.; Hirose, Y. Chem. Lett. 1972, 263-266
94. Pronin, S. V.; Shenvi, R. A. Nat. Chem. 2012, 4, 915-920
95. Yamaguchi, S.; Nedachi, M.; Yokoyama, H.; Hirai, Y. Tetrahedron Lett. 1999, 40, 7363-7365
96. Raczyńska, E. D.; Kosińska, W. Chem. Rev. 2005, 105, 3561-3612
97. Cyrański, M. K. Chem. Rev. 2005, 105, 3773-3811
98. Korth, H.-G.; Mulder, P. J. Org. Chem. 2013, 78, 7674-7682
99. Barton, D. H. R.; Ley, S. V.; Magnus, P. D.; Rosenfeld, M. N. J. Chem. Soc., Perkin Trans. 1 1977, 567-572
100. Crystallographic data for compounds 60 (CCDC 941202), 15- epi-133 (CCDC 941203), and 1 (945867) have previously been reported by us (see ref 28). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
101. Kahne, D. E. Ph.D. Thesis, Columbia University, 1986.
102. White, J. D.; Nolen, E. G., Jr.; Miller, C. H. J. Org. Chem. 1986, 51, 1150-1152
103. White, J. D.; Demnitz, F. W. J.; Xu, Q.; Martin, W. H. C. Org. Lett. 2008, 10, 2833-2836
104. Fitzjarrald, V. P.; Pongdee, R. Tetrahedron Lett. 2007, 48, 3553-3557
105. Alternative batches of material displayed varying diastereomeric ratios ranging from 1:1 to 3:1, favoring the desired C15 spirocycle configuration, albeit in reduced yield, indicating some levels of diastereomeric enhancement during chromatography.
106. Gioeli, C.; Balgobin, N.; Josephson, S.; Chattopadhyaya, J. B. Tetrahedron Lett. 1981, 22, 969-972
107. Corey, E. J.; Yang, Y. K. Tetrahedron Lett. 1992, 33, 2289-2290
108. Nicolaou, K. C.; Reddy, K. R.; Skokotas, G.; Sato, F.; Xiao, X. Y.; Hwang, C. K. J. Am. Chem. Soc. 1993, 115, 3558-3575
109. Denmark, S. E.; Kobayashi, T.; Regens, C. S. Tetrahedron 2010, 66, 4745-4759
110. Fürstner, A.; Weintritt, H. J. Am. Chem. Soc. 1998, 120, 2817-2825
111. Adam, W.; Smerz, A. K. Tetrahedron 1996, 52, 5799-5804
112. Davis, F. A.; Stringer, O. D. J. Org. Chem. 1982, 47, 1774-1775
113. Ikota, N.; Ganem, B. J. Org. Chem. 1978, 43, 1607-1608
114. Clarembeau, M.; Cravador, A.; Dumont, W.; Hevesi, L.; Krief, A.; Lucchetti, J.; Van Ende, D. Tetrahedron 1985, 41, 4793-4812
115. Krief, A.; Hobe, M.; Badaoui, E.; Bousbaa, J.; Dumont, W.; Nazih, A. Synlett 1993, 707-709
116. Santi, C.; Santoro, S.; Testaferri, L.; Tiecco, M. Synlett 2008, 1471-1474
117. Donohoe, T. J.; Blades, K.; Moore, P. R.; Waring, M. J.; Winter, J. J. G.; Helliwell, M.; Newcombe, N. J.; Stemp, G. J. Org. Chem. 2002, 67, 7946-7956
118. Donohoe, T. J.; Bataille, C. J. R. Org. React. 2012, 1-48
119. Phillips, S. T.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 6589-6598
120. Schadt, F. L.; Bentley, T. W.; Schleyer, P. v. R. J. Am. Chem. Soc. 1976, 98, 7667-7674
121. Hlavka, J. J.; Bitha, P.; Boothe, J. H. J. Am. Chem. Soc. 1968, 90, 1034-1037
122. Scott, A. I.; Yamaguchi, E.; Chung, S.-K. Tetrahedron Lett. 1975, 16, 1369-1372
123. Stork, G. Chem. Ind. 1955, 915-916
124. Barton, D. H. R.; Scott, A. I. J. Chem. Soc. 1958, 1767-1772
125. Miller, B. Acc. Chem. Res. 1975, 8, 254-256
126. Horiuchi, C. A.; Ji, S. J.; Matsushita, M.; Chai, W. Synthesis 2004, 202-204
127. Mukaiyama, T.; Matsuo, J.; Kitagawa, H. Chem. Lett. 2000, 29, 1250-1251
128. Tatsuta, K.; Fukuda, T.; Ishimori, T.; Yachi, R.; Yoshida, S.; Hashimoto, H.; Hosokawa, S. Tetrahedron Lett. 2012, 53, 422-425
129. Köster, R.; Seidel, G. In Organometallic Syntheses; King, R. B.; Eisch, J. J., Eds.; Elsevier: Amsterdam, 1998; Vol. 4, pp 440-442.
130. Fürstner, A.; Seidel, G. J. Org. Chem. 1997, 62, 2332-2336
131. Gibert, M.; Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A. Tetrahedron 1997, 53, 8643-8650
132. Nelson, M.; Hillen, W.; Greenwald, R. A. Tetracyclines in Biology, Chemistry, and Medicine; Birkhauser Verlag: Basel, 2001; p 26.
133. Oliva, B.; Gordon, G.; McNicholas, P.; Ellestad, G.; Chopra, I. Antimicrob. Agents Chemother. 1992, 36, 913-919
134. Chopra, I. Antimicrob. Agents Chemother. 1994, 38, 637-640
135. 10 drop in colony-forming units (CFU)/mL.
136. Jenner, L.; Starosta, A. L.; Terry, D. S.; Mikolajka, A.; Filonava, L.; Yusupov, M.; Blanchard, S. C.; Wilson, D. N.; Yusupova, G. Proc. Natl. Acad. Sci., U. S. A. 2013, 110, 3812-3816
137. For a recent review on the role of chemical synthesis in antibacterial drug discovery, see: Wright, P. M.; Seiple, I. B.; Myers, A. G. Angew. Chem., Int. Ed. 2014, 10.1002/anie.201310843