Notoamide E: Biosynthetic incorporation into notoamides C and D in cultures of Aspergillus versicolor NRRL 35600

Tetrahedron Letters

Volumn 52, Issue 16, 2011, Pages 1987-1989

  Finefield, Jennifer M ^a   Greshock, Thomas J ^a   Sherman, David H ^b   Tsukamoto, Sachiko ^c   Williams, Robert M ^a,d  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c KUMAMOTO UNIVERSITY   (Japan)

^d UNIVERSITY OF COLORADO   (United States)

Author keywords

Aspergillus versicolor; Biosynthesis; Prenylated indole alkaloid

Indexed keywords

AMIDE; NOTOAMIDE C; NOTOAMIDE D; NOTOAMIDE E; UNCLASSIFIED DRUG;

ARTICLE; ASPERGILLUS; ASPERGILLUS VERSICOLOR; BIOSYNTHESIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; FUNGAL METABOLISM; FUNGAL STRAIN; FUNGUS CULTURE; ISOTOPE LABELING; NONHUMAN;

ASPERGILLUS VERSICOLOR;

EID: 79952740259     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.078     Document Type: Article

References (25)

1. (a) Birch, A. J.; Wright, J. J. Tetrahedron 1970, 26, 2329;
2. (b) Birch, A. J.; Wright, J. J. S. J. Chem. Soc., Chem. Commun. 1969, 644-645;
3. (c) Birch, A. J.; Russell, R. A. Tetrahedron 1972, 28, 2999.
4. (a) Yamazaki, M.; Okuyama, E.; Kobayashi, M.; Inoue, H. Tetrahedron Lett. 1981, 22, 135-136;
5. (b) Ondeyka, J. G.; Goegelman, R. T.; Schaeffer, J. M.; Kelemen, L.; Zitano, L. J. Antibiot. 1990, 43, 1375-1379;
6. (c) Liesch, J. M.; Wichmann, C. F. J. Antibiot. 1990, 43, 1380-1386;
7. (d) Banks, R. M.; Blanchflower, S. E.; Everett, J. R.; Manger, B. R.; Reading, C. J. Antibiot 1997, 50, 840-846.
8. Qian-Cutrone, J.; Huang, S.; Shu, Y-Z.; Vyas, D.; Fairchild, C.; Menendez, A.; Krampitz, K.; Dalterio, R.; Klohr, S. E.; Gao, Q. J. Am. Chem. Soc. 2002, 124, 14556-14557.
9. (a) Kato, H.; Yoshida, T.; Tokue, T.; Nojiri, Y.; Hirota, H.; Ohta, T.; Williams, R. M.; Tsukamoto, S. Angew. Chem., Int. Ed. 2007, 46, 2254-2256;
10. (b) Tsukamoto, S.; Kato, H.; Samizo, M.; Nojiri, Y.; Onuki, H.; Hirota, H.; Ohta, T. J. Nat. Prod. 2008, 71, 2064-2067;
11. (c) Greshock, T. J.; Grubbs, A. W.; Jiao, P.; Wicklow, D. T.; Gloer, J. B.; Williams, R. M. Angew. Chem., Int. Ed. 2008, 47, 3573-3577;
12. (d) Tsukamoto, S.; Kawabata, T.; Kato, H.; Greshock, T. J.; Hirota, H.; Ohta, T.; Williams, R. M. Org. Lett. 2009, 11, 1297-1300;
13. (e) Tsukamoto, S.; Umaoka, H.; Yoshikawa, K.; Ikeda, T.; Hirota, H. J. Nat. Prod. 2010, 73, 1438-1440.
14. Tsukamoto, S.; Kato, H.; Greshock, T. J.; Hirota, H.; Ohta, T.; Williams, R. M. J. Am. Chem. Soc. 2009, 131, 3834-3835.
15. (a) Grubbs, A. W.; Artman, G. D., (III); Tsukamoto, S.; Williams, R. M. Angew. Chem., Int. Ed. 2007, 46, 2257-2261;
16. (b) Greshock, T. J.; Grubbs, A. W.; Tsukamoto, S.; Williams, R. M. Angew. Chem., Int. Ed. 2007, 46, 2262-2265.
17. (a) Williams, R. M. Chem. Pharm. Bull. 2002, 50, 711-740;
18. (b) Williams, R. M.; Cox, R. J. Acc. Chem. Res. 2003, 36, 127-139;
19. (c) Stocking, E. M.; Sanz-Cervera, J. F.; Williams, R. M. Angew. Chem. 2001, 113, 1336-1338.
20. Angew. Chem., Int. Ed. 2001, 40, 1296-1298..
21. (a) Stocking, E. M.; Williams, R. M.; Sanz-Cervera, J. F. J. Am. Chem. Soc. 2000, 122, 9089-9098;
22. (b) Stocking, E. M.; Sanz-Cervera, J. F.; Unkefer, C. J.; Williams, R. M. Tetrahedron 2001, 57, 5302-5303.
23. (a) Stocking, E. M.; Sanz-Cervera, J. F.; Williams, R. M. Angew. Chem., Int. Ed. 2001, 40, 1296-1298;
24. (b) Ding, Y.; Greshock, T. J.; Miller, K. A.; Sherman, D. H.; Williams, R. M. Org. Lett. 2008, 10, 4863-4866.
25. Calculated according to the method outlined in: Lambert, J. B.; Shurvell, H. B.; Lightner, D. A.; Cooks, R. G. Organic Structural Spectroscopy; Prentice Hall: Upper Saddle River, NJ, 1998. pp. 447-448.