Study on the biosynthesis of the notoamides: Pinacol-type rearrangement of the isoprenyl unit in deoxybrevianamide e and 6-hydroxydeoxybrevianamide e

Tetrahedron Letters

Volumn 52, Issue 51, 2011, Pages 6923-6926

  Kato, Hikaru ^a   Nakamura, Yuichi ^a   Finefield, Jennifer M ^b   Umaoka, Hideharu ^a   Nakahara, Takashi ^a   Williams, Robert M ^b,c   Tsukamoto, Sachiko ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b Department of Ecosystem Science and Sustainability   (United States)

^c UNIVERSITY OF COLORADO CANCER CENTER   (United States)

Author keywords

Aspergillus sp.; Biosynthesis; Prenylated indole alkaloids

Indexed keywords

INDOLE ALKALOID;

ARTICLE; ASPERGILLUS; BIOSYNTHESIS; ISOPRENYLATION; METABOLITE; PINACOL REARRANGEMENT;

ASPERGILLUS SP.;

EID: 81255214507     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.10.065     Document Type: Article

References (23)

1. A.J. Birch, and J.J. Wright Tetrahedron 26 1970 2329
2. A.J. Birch, and J.J.S. Wright J. Chem. Soc., Chem. Commun. 1969 644 645
3. A.J. Birch, and R.A. Russell Tetrahedron 28 1972 2999
4. M. Yamazaki, E. Okuyama, M. Kobayashi, and H. Inoue Tetrahedron Lett. 22 1981 135 136
5. J.G. Ondeyka, R.T. Goegelman, J.M. Schaeffer, L. Kelemen, and L. Zitano J. Antibiot. 43 1990 1375 1379
6. J.M. Liesch, and C.F. Wichmann J. Antibiot. 43 1990 1380 1386
7. R.M. Banks, S.E. Blanchflower, J.R. Everett, B.R. Manger, and C. Reading J. Antibiot. 50 1997 840 846
8. J. Qian-Cutrong, S. Huang, Y.-Z. Shu, D. Vyas, C. Fairchild, A. Menendez, K. Krampitz, R. Dalterio, S.E. Klohr, and Q. Gao J. Am. Chem. Soc. 124 2002 14556 14557
9. S. Martinez-Luis, R. Rodriguez, L. Acevedo, M.C. Gonzalez, A. Lira-Rocha, and R. Mata Tetrahedron 62 2006 1817 1822
10. M. Figueroa, M. Del Carmen González, and R. Mata Nat. Prod. Res. 22 2008 709 714
11. J. Polonsky, M.-A. Merrien, T. Prange, and C. Pascard J. Chem. Soc., Chem. Commun. 1980 601 602
12. T. Prange, M.-A. Billion, M. Vuilhorgne, C. Pascard, and J. Polonsky Tetrahedron Lett. 22 1981 1977 1980
13. H. Hayashi, Y. Nishimoto, and H. Nozaki Tetrahedron Lett. 38 1997 5655 5658
14. H. Kato, T. Yoshida, T. Tokue, Y. Nojiri, H. Hirota, T. Ohta, R.M. Williams, and S. Tsukamoto Angew. Chem., Int. Ed. 46 2007 2254 2256
15. S. Tsukamoto, H. Kato, M. Samizo, Y. Nojiri, H. Onuki, H. Hirota, and T. Ohta J. Nat. Prod. 71 2008 2064 2067
16. T.J. Greshock, A.W. Grubbs, P. Jiao, D.T. Wicklow, J.B. Gloer, and R.M. Williams Angew. Chem., Int. Ed. 47 2008 3573 3577
17. S. Tsukamoto, T. Kawabata, H. Kato, T.J. Greshock, H. Hirota, T. Ohta, and R.M. Williams Org. Lett. 11 2009 1297 1300
18. S. Tsukamoto, H. Kato, T.J. Greshock, H. Hirota, T. Ohta, and R.M. Williams J. Am. Chem. Soc. 131 2009 3834 3835
19. S. Tsukamoto, H. Umaoka, K. Yoshikawa, T. Ikeda, and H. Hirota J. Nat. Prod. 73 2010 1438 1440
20. A.W. Grubbs, G.D. Artman III, S. Tsukamoto, and R.M. Williams Angew. Chem., Int. Ed. 46 2007 2257 2261
21. T.J. Greshock, A.W. Grubbs, S. Tsukamoto, and R.M. Williams Angew. Chem., Int. Ed. 46 2007 2262 2265
22. J.M. Finefield, D.H. Sherman, S. Tsukamoto, and R.M. Williams J. Org. Chem. 76 2011 5954 5958
23. K.A. Miller, S. Tsukamoto, and R.M. Williams Nat. Chem. 1 2009 63 68