New insights into cyclobutenone rearrangements: A total synthesis of the natural ROS-generating anti-cancer agent cribrostatin 6

Chemistry - A European Journal

Volumn 17, Issue 49, 2011, Pages 13698-13705

  Mohamed, Mubina ^a   Gonçalves, Théo P ^a   Whitby, Richard J ^a   Sneddon, Helen F ^b   Harrowven, David C ^a  

^a UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

density functional calculations; flow chemistry; Hammett correlation; reaction mechanisms; thermochemistry

Indexed keywords

ANTI-CANCER AGENTS; ANTI-MICROBIAL AGENT; CCSD; CONTINUOUS-FLOW; FLOW CHEMISTRY; HAMMETT CORRELATION; RATE DETERMINING STEP; REACTION MECHANISM; TOTAL SYNTHESIS; TRANSITION STATE;

DENSITY FUNCTIONAL THEORY; RATE CONSTANTS; THERMOCHEMISTRY;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; CRIBROSTATIN 6; CYCLOBUTANE DERIVATIVE; CYCLOBUTENONE; ISOQUINOLINE DERIVATIVE; REACTIVE OXYGEN METABOLITE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; METABOLISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; CYCLOBUTANES; ISOQUINOLINES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; REACTIVE OXYGEN SPECIES;

EID: 82455219453     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102263     Document Type: Article

References (45)

1. H. W. Moore, S. T. Perri, J. Org. Chem. 1988, 53, 996-1003
2. S. T. Perri, H. J. Dyke, H. W. Moore, J. Org. Chem. 1989, 54, 2032-2034
3. A. Enhsen, K. Karabelas, J. M. Heerding, H. W. Moore, J. Org. Chem. 1990, 55, 1177-1185
4. J. M. Heerding, H. W. Moore, J. Org. Chem. 1991, 56, 4048-4050
5. M. P. Winters, M. Stranberg, H. W. Moore, J. Org. Chem. 1994, 59, 7572-7574
6. H. W. Moore, O. H. W. Decker, Chem. Rev. 1986, 86, 821-830
7. M. W. Reed, D. J. Pollart, S. T. Perri, L. D. Foland, H. W. Moore, J. Org. Chem. 1988, 53, 2477-2482.
8. A. G. Birchler, F. Liu, L. S. Liebeskind, J. Org. Chem. 1994, 59, 7737-7745
9. D. Zhang, I. Llorente, L. S. Liebeskind, J. Org. Chem. 1997, 62, 4330-4338
10. S. Zhang, L. S. Liebeskind, J. Org. Chem. 1999, 64, 4042-4049.
11. R. L. Danheiser, G. B. Dudley, W. F. Austin, in Science in Synthesis, Vol. 23, (Ed.:, R. Danheiser,), Thieme Chemistry, Stuttgart, 2006, pp. 493-568; see also
12. D. C. Harrowven, D. D. Pascoe, D. Demurtas, H. O. Bourne, Angew. Chem. 2005, 117, 1247-1248
13. Angew. Chem. Int. Ed. 2005, 44, 1221-1222
14. D. C. Harrowven, D. D. Pascoe, I. L. Guy, Angew. Chem. 2007, 119, 429-432
15. Angew. Chem. Int. Ed. 2007, 46, 425-428.
16. L. P. Hammett, Physical Organic Chemistry, 2 nd ed., McGraw-Hill, New York, 1970
17. O. Exner, Correlation Analysis of Chemical Data, Plenum Press, New York, 1988.
18. G. R. Pettit, J. C. Collins, J. C. Knight, D. L. Herald, R. A. Nieman, M. D. Williams, R. K. Pettit, J. Nat. Prod. 2003, 66, 544-547
19. R. K. Pettit, B. R. Fakoury, J. C. Knight, C. A. Weber, G. R. Pettit, G. D. Cage, S. Pon, J. Med. Microbiol. 2004, 53, 61-65.
20. S. Nakahara, A. Kubo, Heterocycles 2004, 63, 2355-2362.
21. S. Nakahara, A. Kubo, Y. Mikami, J. Ito, Heterocycles 2006, 68, 515-520.
22. M. D. Markey, T. R. Kelly, J. Org. Chem. 2008, 73, 7441-7443.
23. D. Knueppel, S. F. Martin, Angew. Chem. 2009, 121, 2607-2609
24. Angew. Chem. Int. Ed. 2009, 48, 2569-2571.
25. The flow system employed is shown in Figure 2 of, S. V. Ley, I. R. Baxendale, Chimia 2008, 62, 162-168. Further details may be found on the manufacturer's web site accessed 21/7/2011.
26. A. Odedra, P. H. Seebergera, Angew. Chem. 2009, 121, 2737-2740
27. Angew. Chem. Int. Ed. 2009, 48, 2699-2702
28. F. E. Valera, M. Quaranta, A. Moran, J. Blacker, A. Armstrong, J. Cabral, D. G. Blackmond, Angew. Chem. 2010, 122, 2530-2537
29. Angew. Chem. Int. Ed. 2010, 49, 2478-2485.
30. V. P. Andreev, Chem. Heterocycl. Compd. 2010, 46, 184-195
31. E. Kutter, C. Hansch, J. Med. Chem. 1969, 12, 647-651
32. T. Fujita, C. Takayama, M. Nakajima, J. Org. Chem. 1973, 38, 1623-1630
33. G. Ananchenko, E. Beaudoin, D. Bertin, D. Gigmes, P. Lagarde, S. R. A. Marque, E. Revalor. P. Tordo, J. Phys. Org. Chem. 2006, 19, 269-275.
34. Gaussian 09, Revision A.02, Frisch M.J., G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, N. J. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, Ö. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, Gaussian, Inc., Wallingford CT, 2009.
35. P. W. Musch, C. Remenyi, H. Helten, B. Engels, J. Am. Chem. Soc. 2002, 124, 1823-1828
36. P. R. Schreiner, B. H. Bui, Eur. J. Org. Chem. 2006, 1162-1165
37. P. W. Musch, B. Engels, J. Am. Chem. Soc. 2001, 123, 5557-5562.
38. A. R. Allouche, J. Comput. Chem 2011, 32, 174-182).
39. Programme used: GAMESS(US), ver. 1-Oct-2010 (R1):, M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347-1363.
40. P. Piecuch, S. A. Kucharski, K. Kowalski, M. Musial, Comp. Phys. Commun. 2002, 149, 71-96.
41. S. T. Perri, L. D. Foland, O. H. Decker, H. W. Moore, J. Org. Chem. 1986, 51, 3067-3068.
42. M. T. Hoyt, R. Palchaudhuri, P. J. Hergenrother, Invest. New Drugs 2010, DOI:, accessed 1/12/2010.
43. Z. Jiajie, Chinese Pat. CN101239978(A)
44. S. Ramsbeck, U. Heiser, M. Buchholz, A. J. Niestroj, US Pat. US2008/234313 A1, 2008). In our hands, isolation of amine 15 from that reaction proved difficult, prompting a switch to alane.
45. A. H. Schmidt, G. Kircher, S. Maus, H. Bach, J. Org. Chem. 1996, 61, 2085-2094.