Exploiting the facile release of trifluoroacetate for the α-methylenation of the sterically hindered carbonyl groups on (+)-sclareolide and (-)-eburnamonine

Journal of Organic Chemistry

Volumn 76, Issue 10, 2011, Pages 3676-3683

  Riofski, Mark V ^a   John, Jinu P ^a   Zheng, Mary M ^b   Kirshner, Julia ^b   Colby, David A ^a,b,c  

^a PURDUE UNIVERSITY   (United States)

^b PURDUE UNIVERSITY   (United States)

^c PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL EVALUATION; BREAST CANCER CELLS; CARBONYL GROUPS; EFFICIENT METHOD; METHYLENATION; NATURAL PRODUCTS; SEMI-SYNTHETIC DERIVATIVES; STERIC HINDRANCES; TIME COURSE; TRIFLUOROACETATES;

AMIDES; FUNCTIONAL GROUPS; KETONES; OLEFINS;

CARBONYLATION;

1,3 BENZODIOXOLY VINYL KETONE; 11 METHYLENE SCLAREOLIDE; 2 METHYL 1 PHENYLPROP 2 ENE 1 ONE; 2 METHYLENE 1 INDANONE; 2,7 DIMETHYLENE TROPINONE; 4 CHLOROPHENYL VINYL KETONE; 5 HEXYL 3 METHYLENEDIHYDROFURAN 2(3H) ONE; ADAMANTYL VINYL KETONE; ALPHA METHYLENE 2 OXABICYCLO[3.3.0]OCT 6 EN 3 ONE; ALPHA METHYLENE CAMPHOR; ALPHA METHYLENE CARVONE; ALPHA METHYLENE EBURNAMONINE; ALPHA METHYLENE TERT BUTYL DIMETHYLSILYL ANDOSTERONE; ALPHA METHYLENE TERT BUTYL DIMETHYLSILYL PREGNENOLONE; ALPHA METHYLENE THUJONE; ANDROSTERONE DERIVATIVE; ANTINEOPLASTIC AGENT; CARBONYL DERIVATIVE; N TERT BUTYLCARBAMATE 2 METHYLENE EPSILON CAPROLACTAM; NAPHTHYL VINYL KETONE; PARTHENOLIDE; PHENYL VINYL KETONE; PREGNENOLONE DERIVATIVE; SCLAEROLIDE DERIVATIVE; SCLAREOLIDE; TETRAHYDRO 3 ISOPROPYL 7A METHYL 6 METHYLENEPYRROLO[2,1 B]OXAZOL 5(6H) ONE; THIENYL VINYL KETONE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG; VINBURNINE; VINBURNINE DERIVATIVE;

ARTICLE; BREAST CANCER; CARBON NUCLEAR MAGNETIC RESONANCE; CELL PROLIFERATION; CLINICAL PROTOCOL; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORINE NUCLEAR MAGNETIC RESONANCE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HUMAN; HUMAN CELL; IN VITRO STUDY; METHYLATION; OLEFINATION; PROTON NUCLEAR MAGNETIC RESONANCE;

CELL LINE, TUMOR; DITERPENES; HUMANS; INHIBITORY CONCENTRATION 50; KETONES; METHANE; TRIFLUOROACETIC ACID; VINCA ALKALOIDS;

EID: 79956089567     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo102114f     Document Type: Article

References (55)

1. Staub, I.; Sieber, S. A. J. Am. Chem. Soc. 2009, 131, 6271-6276
2. Weerapana, E.; Simon, G. M.; Cravatt, B. F. Nat. Chem. Biol. 2008, 4, 405-407
3. Sadaghiani, A. M.; Verhelst, S. H. L.; Gocheva, V.; Hill, K.; Majerova, E.; Stinson, S.; Joyce, J. A.; Bogyo, M. Chem. Biol. 2007, 14, 499-511
4. Drahl, C.; Cravatt, B. F.; Sorensen, E. J. Angew. Chem., Int. Ed. 2005, 44, 5788-5809
5. Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426-9451
6. Elford, T. G.; Ulaczyk-Lesanko, A.; De Pascale, G.; Wright, G. D.; Hall, D. G. J. Comb. Chem. 2009, 11, 155-168
7. Zhang, K.; El Damaty, S.; Fasan, R. J. Am. Chem. Soc. 2011, 133, 3242-3245
8. Liu, W.; Groves, J. T. J. Am. Chem. Soc. 2010, 132, 12847-12849
9. Alvarez-Manzaneda, E.; Chahboun, R.; Alvarez, E.; Cano, M. J.; Haidour, A.; Alvarez-Manzaneda, R. Org. Lett. 2010, 12, 4450-4453
10. George, J. H.; Baldwin, J. E.; Adlington, R. M. Org. Lett. 2010, 12, 2394-2397
11. Boukouvalas, J.; Wang, J.-X. Org. Lett. 2008, 10, 3397-3399
12. Margaros, I.; Montagnon, T.; Vassilikogiannakis, G. Org. Lett. 2007, 9, 5585-5588
13. Recent examples in total synthesis: Nakamura, T.; Tsuboi, K.; Oshida, M.; Nomura, T.; Nakazaki, A.; Kobayashi, S. Tetrahedron Lett. 2009, 50, 2835-2839
14. Yang, H.; Qiao, X.; Li, F.; Ma, H.; Xie, L.; Xu, X. Tetrahedron Lett. 2009, 50, 1110-1112
15. Yu, J. S.; Wiemer, D. F. J. Org. Chem. 2007, 72, 6263-6265
16. Lee, K.; Jackson, J. A.; Wiemer, D. F. J. Org. Chem. 1993, 58, 5967-5971
17. Krohn, K.; Riaz, M. Tetrahedron Lett. 2004, 45, 293-294
18. Murray, A. W.; Reid, R. G. Synthesis 1985, 35-38
19. Grieco, P. A.; Pogonowski, C. S. J. Org. Chem. 1974, 39, 1958-1959
20. Ueno, Y.; Setoi, H.; Okawara, M. Tetrahedron Lett. 1978, 19, 3753-3756
21. Grieco, P. A.; Hiroi, K. J. Chem. Soc., Chem. Commun. 1973, 500-501
22. Martin, J.; Watts, P. C.; Johnson, F. J. Org. Chem. 1974, 39, 1676-1681
23. Ksander, G. M.; McMurry, J. E. Tetrahedron Lett. 1976, 17, 4691-4694
24. Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. J. Org. Chem. 1990, 55, 1959-1964
25. Fioravanti, S.; Pellacani, L.; Ramadori, F.; Tardella, P. A. Tetrahedron Lett. 2007, 48, 7821-7824
26. Sloop, J. C.; Bumgardner, C. L.; Washington, G.; Loehle, W. D.; Sankar, S. S.; Lewis, A. B. J. Fluorine Chem. 2006, 127, 780-786
27. Le, Q. T. H.; Umetani, S.; Suzuki, M.; Matsui, M. J. Chem. Soc., Dalton Trans. 1997, 643-647
28. Eisch, J. J.; Dua, S. K.; Behrooz, M. J. Org. Chem. 1985, 50, 3674-3676
29. Engman, L. J. Org. Chem. 1988, 53, 4031-4037
30. Flynn, G. A.; Lee, S. A.; Faris, M.; Brandt, D. W.; Charkravarty, S. Patent WO 2007136790, November 29, 2007.
31. Augelli-Szafran, C. E.; Wolfe, M. S.; Wei, H. Patent WO 2009051661, April 23, 2009.
32. 13C 5.10/93.9, 5.10/65.3, 5.10/42.3, 4.70/93.9, 4.70/65.3, 4.70/, 4.28/93.9, 4.28/87.1, 4.28/65.3, 3.54/93.9, 3.54/87.1, 3.54/42.3.
33. Kinsho, T.; Watanabe, T.; Ohashi, M.; Hasegawa, K.; Tachibana, S. U.S. Patent 7,531,289, May 12, 2009.
34. Polshettiwar, V.; Varma, R. S. J. Org. Chem. 2007, 72, 7420-7422
35. Smith, A. B.; Dorsey, B. D.; Ohba, M.; Lupo, A. T.; Malamas, M. S. J. Org. Chem. 1988, 53, 4314-4325
36. Martínez-Ramos, F.; Vargas-Díaz, M. E.; Chacón-García, L.; Tamariz, J.; Joseph-Nathan, P.; Zepeda, L. G. Tetrahedron: Asymmetry 2001, 12, 3095-3103
37. Otrubova, K.; Lushington, G.; Vander Velde, D.; McGuire, K. L.; McAlpine, S. R. J. Med. Chem. 2008, 51, 530-544
38. Ramachandran, P. V.; Pratihar, D.; Nair, H. N. G.; Walters, M.; Smith, S.; Yip-Schneider, M. T.; Wu, H.; Schmidt, C. M. Bioorg. Med. Chem. Lett. 2010, 20, 6620-6623
39. Nakagawa, Y.; Iinuma, M.; Matsuura, N.; Yi, K.; Naoi, M.; Nakayama, T.; Nozawa, Y.; Akao, Y. J. Pharmacol. Sci. 2005, 97, 242-252
40. Kwok, B. H. B.; Koh, B.; Ndubuisi, M. I.; Elofsson, M.; Crews, C. M. Chem. Biol. 2001, 8, 759-766
41. Jakubik, J.; Bacakova, L.; El-Fakahany, E. E.; Tucek, S. Mol. Pharmacol. 1997, 52, 172-179
42. Gan, C.-Y.; Low, Y.-Y.; Etoh, T.; Hayashi, M.; Komiyama, K.; Kam, T.-S. J. Nat. Prod. 2009, 72, 2098-2103
43. Chen, J.; Lu, L.; Feng, Y.; Wang, H.; Dai, L.; Li, Y.; Zhang, P. Cancer Lett. 2011, 300, 48-56
44. 13C NMR, IR, and HRMS. Melting point and optical rotation were also measured as needed.
45. Guan, B.; Xing, D.; Cai, G.; Wan, X.; Yu, N.; Fang, Z.; Yang, L.; Shi, Z. J. Am. Chem. Soc. 2005, 127, 18004-18005
46. Itoh, K.; Nakanishi, S.; Otsuji, Y. Bull. Chem. Soc. Jpn. 1991, 64, 2965-2977
47. Matsuo, J. -I.; Aizawa, Y. Chem. Commun. 2005, 2399-2401
48. Kang, S. K.; Ho, P. S.; Yoon, S. K.; Lee, J. C.; Lee, K. J. Synthesis 1998, 823-825
49. Tonari, K.; Matsumoto, N. J. Oleo Sci. 2002, 51, 255-258
50. Rodrigues, J.; Siqueira-Filho, E.; Mancilha, M.; Moran, P. Synth. Commun. 2003, 33, 331-340
51. Crich, D.; Chen, C.; Hwang, J. T.; Yuan, H.; Papadatos, A.; Walter, R. J. Am. Chem. Soc. 1994, 116, 8937-8951
52. Choudhuryi, P. K.; Foubelo, F.; Yus, M. Tetrahedron 1999, 55, 10779-10788
53. Badio, B.; Garraffo, H. M.; Plummer, C. V.; Padgett, W. L.; Daly, J. W. Eur. J. Pharmacol. 1997, 321, 189-194
54. Drew, J.; Letellier, M.; Morand, P.; Szabo, A. G. J. Org. Chem. 1987, 52, 4047-4052
55. Izzo, I.; Di Filippo, M.; Napolitano, R.; De Riccardis, F. Eur. J. Org. Chem. 1999, 3505-3510