Enantioselective total synthesis and biological evaluation of (+)-kibdelone A and a tetrahydroxanthone analogue

Journal of Organic Chemistry

Volumn 78, Issue 15, 2013, Pages 7617-7626

  Winter, Dana K ^a   Endoma Arias, Mary Ann ^b   Hudlicky, Tomas ^b   Beutler, John A ^c   Porco, John A ^a  

^a Boston University   (United States)

^b BROCK UNIVERSITY   (Canada)

^c NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; BIOLOGICAL EVALUATION; DIHYDROXYLATION; ELECTROCYCLIZATION; ENANTIOSELECTIVE TOTAL SYNTHESIS; ONE POT; TOTAL SYNTHESIS;

CHEMISTRY; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

KIBDELONE A; TETRAHYDROXANTHONE DERIVATIVE; UNCLASSIFIED DRUG; XANTHONE DERIVATIVE;

ARTICLE; ARYLATION; CYCLIZATION; DIHYDROXYLATION; ENANTIOSELECTIVITY; FRIEDEL CRAFTS REACTION; MICHAEL ADDITION; SYNTHESIS;

EID: 84881246659     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo401169z     Document Type: Article

References (39)

1. Roberts, J. C. Chem. Rev. 1961, 61, 591-605
2. Peres, V.; Nagem, T. J; de Oliviera, F. F. Phytochemistry 2000, 55, 683-710
3. Pinto, M.; Sousa, E.; Nascimento, M. Curr. Med. Chem. 2005, 12, 2517-2538
4. Masters, K.-S.; Bräse, S. Chem. Rev. 2012, 112, 3717-3776
5. Winter, D. K.; Sloman, D. L.; Porco, J. A., Jr. Nat. Prod. Rep. 2013, 30, 382-391
6. Turner, P. A.; Griffin, E. M.; Whatmore, J. L.; Shipman, M. Org. Lett. 2011, 13, 1056-1059
7. Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. Chem.-Eur. J. 2007, 13, 1610-1619
8. Sloman, D. L.; Mitasev, B.; Scully, S. S.; Beutler, J. A.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2011, 50, 2511-2515
9. Sloman, D. L; Bacon, J. W.; Porco, J. A., Jr. J. Am. Chem. Soc. 2011, 133, 9952-9955
10. Masuo, R.; Ohmori, K.; Hintermann, L.; Yoshida, S.; Suzuki, K. Angew. Chem., Int. Ed. 2009, 48, 3462-3465
11. Butler, J. R.; Wang, C.; Bian, J.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 9956-9959
12. Endoma-Arias, M. A. A.; Hudlicky, T. Tetrahedron Lett. 2011, 52, 6632-6634
13. Semak, V.; Metcalf, T. A.; Endoma-Arias, M. A. A.; Mach, P.; Hudlicky, T. Org. Biomol. Chem. 2012, 10, 4407-4416
14. Bégué, J.-P.; Bonnet-Delpon, D.; Crousse, B. Synlett 2004, 18-29
15. Shuklov, I. A.; Dubrovina, N. V.; Börner, A. Synthesis 2007, 2925-2943
16. Dohi, T.; Washimi, N.; Kamitanaka, T.; Fukushima, K.-i.; Kita, Y. Angew. Chem., Int. Ed. 2011, 50, 6142-6146
17. Pastine, S. J.; Youn, S. W.; Sames, D. Org. Lett. 2003, 5, 1055-1058
18. Mamane, V.; Hannen, P.; Fürstner, A. Chem.-Eur. J. 2004, 10, 4556-4575
19. Nevado, C.; Echavarren, A. M. Synthesis 2005, 167-182
20. Komeyama, K.; Igawa, R.; Takaki, K. Chem. Commun. 2010, 46, 1748-1750
21. Merlic, C. A.; Pauly, M. E. J. Am. Chem. Soc. 1996, 118, 11319-11320
22. Miura, T.; Murata, H.; Kiyota, K.; Kusama, J.; Iwasawa, N. J. Mol. Catal. A.: Chem. 2004, 213, 59-71
23. Sangu, K.; Fuchibe, K.; Akiyama, T. Org. Lett. 2004, 6, 353-355
24. de Mendoza, P.; Echavarren, A. M. Pure Appl. Chem. 2010, 82, 801-820
25. Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769-3775
26. Talele, H. R.; Gohil, J.; Bedekar, A. V. Bull. Chem. Soc. Jpn. 2009, 82, 1182-1186
27. Kelly, R.; Jagoe, C. T.; Li, Q. J. Am. Chem. Soc. 1989, 111, 4522-4524
28. Mehta, G.; Shah, S. R. Tetrahedron Lett. 1991, 32, 5195-5198
29. Mehta, G.; Shah, S. R.; Venkateswarlu, Y. Tetrahedron 1994, 50, 11729-11742
30. Hernandez-Perez, A. C.; Vlassova, A.; Collins, S. Org. Lett. 2012, 14, 2988-2991
31. Nakano, A.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Org. Lett. 2006, 8, 5357-5360
32. Nakano, A.; Kawahara, S.; Akamatsu, S.; Morokuma, K.; Nakatani, M.; Iwabuchi, Y.; Takahashi, K.; Ishihara, J.; Hatakeyama, S. Tetrahedron 2006, 62, 381-389
33. Gibson, D. T.; Hensley, M.; Yoshioka, H.; Mabry, T. J. Biochemistry 1970, 9, 1626-1630
34. For the report of a recombinant organism, see: Zylskra, G. J.; Gibson, D. T. J. Biol. Chem. 1989, 264, 14940-14946
35. For medium-scale fermentation protocols, see: Endoma, M. A. A.; Bai, V. P.; Hansen, J.; Hudlicky, T. Org. Process Res. Dev. 2002, 6, 525-532
36. Boyd, D. R.; Sharma, N. D.; Byrne, B. E.; Haughey, S. A.; Kennedy, M. A.; Allen, C. C. R. Org. Biomol. Chem. 2004, 2, 2530-2537
37. Oda, K.; Nishimoto, N.; Tamai, Y.; Yamaguchi, Y.; Yoshimura, T.; Wada, K.; Machida, M. Heterocycles 2005, 65, 1985-1988
38. Pelter, A.; Elgendy, S. M. A. J. Chem. Soc., Perkin Trans. 1 1993, 1891-1896
39. Dallaire, C.; Brook, M. A. Organometallics 1993, 12, 2332-2338