Enantioselective total synthesis of ( - )-kibdelone C

Journal of the American Chemical Society

Volumn 133, Issue 26, 2011, Pages 9956-9959

  Butler, John R ^a   Wang, Chao ^a   Bian, Jianwei ^a   Ready, Joseph M ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; ENANTIOSELECTIVE TOTAL SYNTHESIS; HUMAN CANCER CELLS; NATURAL PRODUCTS; POLYKETIDES; RING SYSTEMS; SHI EPOXIDATION;

AROMATIC COMPOUNDS; CELL CULTURE; KETONES; REACTION KINETICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CYCLIZATION;

ACID; ANTINEOPLASTIC AGENT; CARBON; HYDROGEN; KIBDELONE C; TETRAHYDROXANTHONE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; ARYLATION; CATALYSIS; COVALENT BOND; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVE TOTAL SYNTHESIS; ENANTIOSELECTIVITY; EPOXIDATION; HYDROGEN BOND; SHI EPOXIDATION; STEREOCHEMISTRY;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CHEMISTRY TECHNIQUES, SYNTHETIC; HUMANS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; XANTHONES;

EID: 79959863573     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja204040k     Document Type: Article

References (35)

1. Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. J. Chem. Eur. J. 2007, 13, 1610
2. Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. J. Org. Lett. 2006, 8, 5267
3. Prasad, K. S.; Nayak, R. FEBS Lett. 1976, 71, 171
4. Latham, M. D.; King, C. K.; Gorycki, P.; Macdonald, T. L.; Ross, W. E. Cancer Chemother. Pharmacol. 1989, 24, 167
5. Capranico, G.; Ferri, F.; Fogli, M. V.; Russo, A.; Lotito, L.; Baranello, L. Biochimie 2007, 89, 482
6. Lee, T. M.; Carter, G. T.; Borders, D. B. J. Chem. Soc., Chem. Commun. 1989, 1771
7. Nakagawa, A.; Oura, S. J. Antibiot. 1987, 40, 301
8. Someno, T.; Kunimoto, S.; Nakamura, H.; Naganawa, H.; Ikeda, D. J. Antibiot. 2005, 58, 56
9. Chu, M.; Truumees, I.; Mierzwa, R.; Terracciano, J.; Patel, M.; Loebenberg, D.; Kaminski, J. J.; Das, P.; Puar, M. S. J. Nat. Prod. 1997, 60, 525
10. Simaomicin α synergizes with the DNA-damaging agent bleomycin at sub-nanomolar concentrations: Arai, M.; Sato, H.; Kobayashi, H.; Suganuma, M; Kawabe, T.; Tomoda, H.; Omura, S. Biochem. Biophys. Res. Commun. 2004, 317, 817
11. Sloman, D. L.; Mitasev, B.; Scully, S. S.; Beutler, J. A.; Porco, J. A. Angew. Chem., Int. Ed. 2011, 50, 2511
12. Sloman, D. L., Bacon, J. W., and Porco, J. A., Jr. J. Am. Chem. Soc. 2011, 133 DOI: 10.1021/ja203642n (preceding paper in this issue)
13. Cervinomycins: Kelly, T. R.; Jagoe, C. T.; Li, Q. J. Am. Chem. Soc. 1989, 111, 4522
14. Rao, A. V. R.; Yadav, J. S.; Reddy, K. K.; Upender, V. Tetrahedron Lett. 1991, 32, 5199
15. Mehta, G.; Shah, S. R.; Venkateswarlu, Y. Tetrahedron 1994, 50, 11729 TMC-66: Hosokawa, S.; Fumiyama, H.; Fukuda, H.; Fukuda, T.; Seki, M.; Tatsuta, K. Tetrahedron Lett. 2007, 48, 7305 FD-594 Aglycon: Masuo, R.; Ohmori, K.; Hintermann, L.; Yoshida, S.; Suzuki, K. Angew. Chem. Int. Ed. 2009, 48, 3462
16. Johansson, R.; Karlstroem, S.; Kers, A.; Nordvall, G.; Rein, T.; Slivo, C. Int. Pat. WO 2008/039139A1.
17. Barfknecht, C. F.; Nichols, D. E. J. Med. Chem. 1971, 14, 370
18. De Mico, A.; Margarita, R.; Parlanti, L.; Vescovi, A.; Piancatelli, G. J. Org. Chem. 1997, 62, 6974
19. Walker, E. R.; Leung, S. Y.; Barrett, A. G. M. Tetrahedron Lett. 2005, 46, 6537
20. Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729
21. Shi, Y. Acc. Chem. Res. 2004, 37, 488
22. Lim, S. M.; Hill, N.; Myers, A. G. J. Am. Chem. Soc. 2009, 131, 5763
23. Tan, L.; Yasuda, N.; Yoshikawa, N.; Hartner, F. W.; Eng, K. K.; Leonard, W. R.; Tsay, F.-R.; Volante, R. P.; Tillyer, R. D. J. Org. Chem. 2005, 70, 8027
24. Nicolaou, K. C.; Li, A. Angew. Chem. Int. Ed. 2008, 47, 6579
25. Formaldehyde, or its equivalent, arises from deprotection of the MOM group.
26. Soheili, A.; Albaneze-Walker, J.; Murry, J. A.; Dormer, P. G.; Hughes, D. L. Org. Lett. 2003, 5, 4191
27. Fortuitously, iodination was originally attempted on phenol 22 recovered from a failed Cu(II)-mediated phenolic coupling.
28. Cu-catalyzed bromination: Yang, L.; Lu, Z.; Stahl, S. S. Chem. Commun. 2009, 6460
29. Inadvertent iodination in the presence of Cu: Li, X.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500
30. Cu(OH)Cl·TMEDA: Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264
31. Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2005, 128, 581 Reviews: Ackermann, L.; Vicente, R.; Kapdi, A. R. Angew. Chem. Int. Ed. 2009, 48, 9792
32. Gutekunst, W. R.; Baran, P. S. Chem. Soc. Rev. 2011, 40, 1976
33. 3/NCS performed similarly.
34. 1H NMR data are consistent with 30. A similar product was identified during the isolation of 1 - 3. See ref 1.
35. See Supporting Information for full experimental details.