First synthesis of decaturin C, an antiinsectant diterpenoid isolated from Penicillium thiersii

Tetrahedron

Volumn 68, Issue 44, 2012, Pages 9029-9034

  Nakazaki, Kimiharu ^a   Hayashi, Kojiro ^a   Hosoe, Shintaro ^a   Tashiro, Takuya ^b   Kuse, Masaki ^a   Takikawa, Hirosato ^a  

^a KOBE UNIVERSITY   (Japan)

^b RIKEN   (Japan)

Author keywords

Decaturins; Penicillium thiersii; Spiro cyclization; Wieland Miescher ketone

Indexed keywords

DECATURIN C; DITERPENOID; KETONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; PENICILLIUM; PENICILLIUM THIERSII; PRIORITY JOURNAL; ROBINSON ANNULATION; SYNTHESIS;

PENICILLIUM THIERSII;

EID: 84866355804     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.08.067     Document Type: Article

References (19)

1. C. Li, J.B. Gloer, D.T. Wicklow, and P.F. Dowd J. Nat. Prod. 68 2005 319 322
2. Y. Zhang, C. Li, D.C. Swenson, J.B. Gloer, D.T. Wicklow, and P.F. Dowd Org. Lett. 5 2003 773 776
3. R. Ubillas, C.L. Barnes, H. Gracz, G.E. Rottinghaus, and M.S. Tempesta J. Chem. Soc., Chem. Commun. 1989 1618 1619
4. Ubillas, R. Chemical Studies on Penicillium oxalicum, Ph. D. Thesis, University of Missouri-Columbia, 1990; pp 61-74.
5. F.A. Macías, R.M. Varela, A.M. Simonet, H.G. Cutlar, S.J. Cutlar, F.M. Dugan, and R.A. Hill J. Org. Chem. 65 2000 9039 9046
6. F.A. Macías, R.M. Varela, A.M. Simonet, H.G. Cutlar, S.J. Cutlar, S.A. Ross, D.C. Dunbar, F.M. Dugan, and R.A. Hill Tetrahedron Lett. 41 2000 2683 2686
7. S. Omura, H. Tomoda, Y.K. Kim, and H. Nishida J. Antibiot. 46 1993 1168 1169
8. H. Tomoda, Y.K. Kim, H. Nishida, R. Masuma, and S. Omura J. Antibiot. 47 1994 148 153
9. Y.K. Kim, H. Tomoda, H. Nishida, T. Sunazuka, R. Obata, and S. Omura J. Antibiot. 47 1994 154 162
10. H. Takikawa, M. Hirooka, and M. Sasaki Tetrahedron Lett. 43 2002 1713 1716
11. H. Takikawa, M. Hirooka, and M. Sasaki Tetrahedron Lett. 44 2003 5235 5238
12. H. Takikawa, Y. Imamura, and M. Sasaki Tetrahedron 62 2006 39 48
13. S. Hosoe, T. Nakai, M. Sasaki, and H. Takikawa Tetrahedron Lett. 47 2006 4425 4428
14. P. Buchschacher, and A. Fuerst Org. Synth. 63 1985 37 43
15. M. Kim, R.S. Gross, H. Sevestre, N.K. Dunlap, and D.S. Watt J. Org. Chem. 53 1988 93 98
16. C.H. Heathcock, E.G. DelMar, and S.L. Graham J. Am. Chem. Soc. 104 1982 1907 1917
17. L.N. Mander, and S.P. Sethi Tetrahedron Lett. 24 1983 5425 5428
18. S.R. Crabtree, W.L.A. Chu, and L.N. Mander Synlett 1990 169 170
19. N.S. Narashmham, and R. Ammanamanchi J. Org. Chem. 48 1983 3945 3947