Total synthesis, structural elucidation, and structure-cytotoxic activity relationship of (-)-gummiferol

Journal of Organic Chemistry

Volumn 78, Issue 6, 2013, Pages 2443-2454

  Takamura, Hiroyoshi ^a   Wada, Hiroko ^a   Lu, Nan ^a   Ohno, Osamu ^b   Suenaga, Kiyotake ^b   Kadota, Isao ^a  

^a OKAYAMA UNIVERSITY   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; CYTOTOXIC ACTIVITIES; HUMAN CANCER CELLS; NATURAL PRODUCTS; SPECIFIC ROTATIONS; STEREODIVERGENT SYNTHESIS; STRUCTURAL ELEMENTS; STRUCTURAL ELUCIDATION;

STEREOCHEMISTRY;

NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ACETYLENE DERIVATIVE; EPOXIDE; GUMMIFEROL; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CADIOT CHODKIEWICZ REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CYTOTOXICITY; DERIVATIZATION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; HUMAN; HUMAN CELL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

ACETATES; ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; FATTY ALCOHOLS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84875145176     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302665c     Document Type: Article

References (34)

1. Parish, C. A.; Huber, J.; Baxter, J.; González, A.; Collado, J.; Platas, G.; Diez, M. T.; Vicente, F.; Dorso, K.; Abruzzo, G.; Wilson, K. J. Nat. Prod. 2004, 67, 1900
2. Senn, M.; Gunzenhauser, S.; Brun, R.; Séquin, U. J. Nat. Prod. 2007, 70, 1565
3. Tian, Y.; Wei, X.; Xu, H. J. Nat. Prod. 2006, 69, 1241
4. Lerch, M. L.; Harper, M. K.; Faulkner, D. J. J. Nat. Prod. 2003, 66, 667
5. Bernart, M. W.; Cardellina, J. H., II; Balaschak, M. S.; Alexander, M. R.; Shoemaker, R. H.; Boyd, M. R. J. Nat. Prod. 1996, 59, 748
6. Ito, A.; Cui, B.; Chávez, D.; Chai, H.-B.; Shin, Y. G.; Kawanishi, K.; Kardono, L. B. S.; Riswan, S.; Farnsworth, N. R.; Cordell, G. A.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 2001, 64, 246
7. Jung, H.-J.; Min, B.-S.; Park, J.-Y.; Kim, Y.-H.; Lee, H.-K.; Bae, K.-H. J. Nat. Prod. 2002, 65, 897
8. Okamoto, C.; Nakao, Y.; Fujita, T.; Iwashita, T.; van Soest, R. W. M.; Fusetani, N.; Matsunaga, S. J. Nat. Prod. 2007, 70, 1816
9. Fullas, F.; Brown, D. M.; Wani, M. C.; Wall, M. E.; Chagwedera, T. E.; Farnsworth, N. R.; Pezzuto, J. M.; Kinghorn, A. D. J. Nat. Prod. 1995, 58, 1625
10. Nicolaou, K. C.; Snyder, S. A. Angew. Chem., Int. Ed. 2005, 44, 1012
11. Maier, M. E. Nat. Prod. Rep. 2009, 26, 1105
12. Suyama, T. L.; Gerwick, W. H.; McPhail, K. L. Bioorg. Med. Chem. 2011, 19, 6675
13. Takamura, H.; Wada, H.; Lu, N.; Kadota, I. Org. Lett. 2011, 13, 3644
14. Schmidt, B.; Hölter, F. Chem.-Eur. J. 2009, 15, 11948
15. Kotaki, T.; Shinada, T.; Kaihara, K.; Ohfune, Y.; Numata, H. Org. Lett. 2009, 11, 5234
16. Tamura, S.; Ohno, T.; Hattori, Y.; Murakami, N. Tetrahedron Lett. 2010, 51, 1523
17. Urabe, D.; Todoroki, H.; Masuda, K.; Inoue, M. Tetrahedron 2012, 68, 3210
18. Chodkiewicz, W.; Cadiot, P. C. R. Hebd. Seances Acad. Sci. 1955, 241, 1055
19. Brandsma, L. Preparative Acetylenic Chemistry, 2 nd ed.; Elsevier: Amsterdam, 1988.
20. Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2632
21. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5974
22. Hanson, R. M.; Sharpless, K. B. J. Org. Chem. 1986, 51, 1922
23. Zhang, P.; Morken, J. P. J. Am. Chem. Soc. 2009, 131, 12550
24. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719
25. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092
26. Parikh, J. R.; Doering, W. v. E. J. Am. Chem. Soc. 1967, 89, 5505
27. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183
28. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769
29. Díaz, D.; Martín, T.; Martín, V. S. J. Org. Chem. 2001, 66, 7231
30. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1994, 35, 3529
31. González, I. C.; Forsyth, C. J. J. Am. Chem. Soc. 2000, 122, 9099
32. Reber, S.; Knöpfel, T. F.; Carreira, E. M. Tetrahedron 2003, 59, 6813
33. Alami, M.; Ferri, F. Tetrahedron Lett. 1996, 37, 2763
34. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron 1993, 49, 5225