Synthesis of all possible isomers corresponding to the proposed structure of montanacin E, and their antitumor activity

Journal of Organic Chemistry

Volumn 74, Issue 16, 2009, Pages 6382-6385

  Takahashi, Shunya ^a   Takahashi, Ryotaro ^a   Hongo, Yayoi ^a   Koshino, Hiroyuki ^a   Yamaguchi, Kazunori ^b   Miyagi, Taeko ^b  

^a RIKEN   (Japan)

^b MIYAGI CANCER CENTER RESEARCH INSTITUTE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CELL CULTURE; CELL MEMBRANES; ISOMERS;

ANTI-TUMOR ACTIVITIES; CASCADE CYCLIZATION; CHEMICAL EQUATIONS; CROSS METATHESIS; DIASTEREOMERS; HUMAN SOLID TUMOR CELL LINES; INHIBITORY ACTIVITY; SPECTROSCOPIC DATA; STEREOSELECTIVE FORMATION; TETRA-HYDROFURAN; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

([13',18' DIHYDROXY 2',6':14',17' DIOXIDO 8' OXOTRIACONTANYL] 5 METHYLFURAN 2 (5H)ONE; GAMMA LACTONE DERIVATIVE; MONTANACIN E; PLANT EXTRACT; TETRAHYDROFURAN; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; FURAN DERIVATIVE;

ANNONA MONTANA; ANTINEOPLASTIC ACTIVITY; ARTICLE; CYCLIZATION; DIASTEREOISOMER; DRUG INHIBITION; DRUG STRUCTURE; HUMAN; HUMAN CELL; ISOMER; MEDICINAL PLANT; RING CLOSING METATHESIS; SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS; ANIMAL; ARTEMIA; CHEMISTRY; DRUG EFFECTS; IC50; ISOMERISM; TOXICITY; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; ARTEMIA; CELL LINE, TUMOR; FURANS; HUMANS; INHIBITORY CONCENTRATION 50; ISOMERISM;

EID: 70349160765     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901150h     Document Type: Article

References (38)

1. For recent reviews, see: (a) Zafra-Polo, M. C.; Gonzalez, M. C.; Estornell, E.; Sahpaz, S.; Cortes, D. Phytochemistry 1996, 42, 253-271.
2. (b) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Nat. Prod. Rep. 1996, 13, 275-306.
3. Zafra-Polo, M. C.; Figadére, B.; Gallardo, T.; Tormo, J. R.; Cortes, D. Phytochemistry 1998, 48, 1087-1117.
4. Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540.
5. (e) Bermejo, A.; Figadére, B.; Zafra-Polo, M.-C.; Barrachina, I.; Estornell, E.; Cortes, D. Nat. Prod. Rep. 2005, 22, 269-303.
6. (f) McLaughlin, J. L. J. Nat. Prod. 2008, 71, 1311-1321.
7. (a) Shi, G.; Alfonso, D.; Fatope, M. O.; Zeng, L.; Gu, Z.-M.; Zhao, G.-X.; He, K.; MacDougal, J. M.; McLaughlin, J. L. J. Am. Chem. Soc. 1995, 117, 10409-10410.
8. (b) Shi, G.; Kozlowski, J. F.; Schwedler, J. T.; Wood, K. V.; MacDougal, J. M.; McLaughlin, J. L. J. Org. Chem. 1996, 61, 7988-7989.
9. Alali, F. Q.; Rogers, L.; Zhang, Y.; McLaughlin, J. L. Tetrahedron 1998, 54, 5833-5844.
10. Chavez, D.; Acevedo, L. A.; Mata, R. J. Nat. Prod. 1998, 61, 419-421.
11. (e) Fall, D.; Duval, R. A.; Gleye, C.; Laurens, A.; Hocquemiller, R. J. Nat. Prod. 2004, 67, 1041-1043.
12. (a) Wang, L.-Q.; Zhao, W.-M.; Qin, G.-W.; Cheng, K.-F.; Yang, R.-Z. Nat. Prod. Lett. 1999, 14, 83-90.
13. (b) Wang, L.-Q.; Nakamura, N.; Meselhy, M. R.; Hattori, M.; Zhao, W.-M.; Cheng, K.-F.; Yang, R.-Z.; Qin, G.-W. Chem. Pharm. Bull. 2000, 48, 1109-1113.
14. Recent syntheses of THP-THF acetogenins: For jimenezin, see: (a) Hwang, C. H.; Keum, G.; Sohn, K.; Lee, D. H.; Lee, E. Tetrahedron Lett. 2005, 46, 6621-6623.
15. (b) Bandur, N. G.; Brückner, D.; Hoffmann, R. W.; Koert, U. Org. Lett. 2006, 8, 3829-3831.
16. For mucocin, see: (c) Evans, P. A.; Cui, J.; Gharpure, S. J.; Polosukhin, A.; Zhang, H.-R. J. Am. Chem. Soc. 2003, 125, 14702-14703.
17. Crimmins, M. T.; Zhang, Y.; Diaz, F. A. Org. Lett. 2006, 8, 2369-2372.
18. For muconin, see: (e) Yoshimitsu, T.; Makino, T.; Nagaoka, H. J. Org. Chem. 2004, 69, 1993-1998.
19. The numbering system of the carbon follows the one employed in ref 3.
20. The absolute configuration of annonaceous acetogenins has been mainly determined by the modified Mosher's method: Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4093.
21. (a) Takahashi, S.; Nakata, T. Tetrahedron Lett. 1999, 40, 723-726.
22. (b) Takahashi, S.; Nakata, T. Tetrahedron Lett. 1999, 40, 727-730.
23. Takahashi, S.; Maeda, K.; Hirota, S.; Nakata, T. Org. Lett. 1999, 1, 2025-2028.
24. Takahashi, S.; Fujisawa, K.; Sakairi, N.; Nakata, T. Heterocycles 2000, 53, 1361-1370.
25. (e) Takahashi, S.; Nakata, T. J. Org. Chem. 2002, 67, 5739-5752.
26. (f) Takahashi, S.; Kubota, A.; Nakata, T. Angew. Chem., Int. Ed. 2002, 41, 4751-4754.
27. (g) Takahashi, S.; Kubota, A.; Nakata, T. Tetrahedron Lett. 2002, 43, 8661-8664.
28. (h) Takahashi, S.; Kubota, A.; Nakata, T. Tetrahedron 2003, 59, 1627-1638.
29. Takahashi, S.; Kubota, A.; Nakata, T. Org. Lett. 2003, 6, 1353-1356.
30. (j) Takahashi, S.; Ogawa, N.; Koshino, H.; Nakata, T. Org. Lett. 2005, 7, 2783-2786.
31. (k) Takahashi, S.; Hongo, Y.; Ogawa, N.; Koshino, H.; Nakata, T. J. Org. Chem. 2006, 71, 6305-6308.
32. Takahashi, S.; Hongo, Y.; Tsukagoshi, Y.; Koshino, H. Org. Lett. 2008, 10, 4223-4226.
33. Grubbs, R. H. In Handbook of Metathesis; Wiley-VCH: New York, 2003; Vols. 1-3.
34. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483-2547.
35. Sinha, S. C.; Keinan, E. J. Am. Chem. Soc. 1993, 115, 4891-4892.
36. D between 4 or 18 and natural montanacin E provided no reliable information because of the small values and low concentrations reported.
37. Private communication from Prof. G. W. Qin.
38. Shi, G.; Zeng, L.; Gu, Z.-M.; MacDougal, J. M.; McLaughlin, J. L. Heterocycles 1995, 41, 1785-1796.