Jietacins with potent nematocidal activity; Efficient isolation of novel analogs and divergent total synthesis of jietacin A, B, C, and D the paper is dedicated to Professor Iwao Ojima on the occasion of his 70th birthday

Tetrahedron

Volumn 71, Issue 14, 2015, Pages 2149-2157

  Sugawara, Akihiro ^a   Kubo, Masahiko ^a   Nakashima, Takuji ^a   Hirose, Tomoyasu ^a   Tsunoda, Noriaki ^a   Yahagi, Kyoichi ^a   Asami, Yukihiro ^a   Yamada, Takeshi ^a   Shiomi, Kazuro ^a   Takahashi, Yoko ^a   Omura, Satoshi ^a   Sunazuka, Toshiaki ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

Grignard reaction; Isolation; Structure elucidation; Total synthesis; Vinyl azoxy

Indexed keywords

1 BROMO 6 METHYLOCTANE; 2 (DODECYLDIAZENYL)ETHANOL; 6 METHYLOCTANOL; 8 [ (2' HYDROXYETHYL) NNO AZOXY] N METHYL N METHYLOCTANAMIDE; 8 [ (2' HYDROXYETHYL) ONN AZOXYL] N METHOXY N METHYLOCTANAMIDE 21; 8 [(2' HYDROXYETHYL)DIAZENYL] N METHOXY N METHYLOCTANAMIDE; 8 [(2' TRIETHYLSILYLHYDROXYETHYL)DIAZENYL] N METHOXY N METHYLOCTANAMIDE; 8 [VINYL ONN AZOXY] N METHOXY N METHYLOCTANAMIDE; ANTINEMATODAL AGENT; JIETACIN A; JIETACIN B; JIETACIN C; JIETACIN D; NATURAL PRODUCT; NBETA (BENZYLOXYCARBONYL) NALPHA (DODECYL) NBETA (2 HYDROXYETHYL)HYDRAZIDE; NBETA (BENZYLOXYCARBONYL) NALPHA (METHYLOCTANOATE) NBETA (2 HYDROXYETHYL)HYDRAZIDE; NBETA (BENZYLOXYCARBONYL) NALPHA (N METHOXY N METHYLOCTANAMIDE) NBETA (2 HYDROXYETHYL)HYDRAZIDE; UNCLASSIFIED DRUG;

ARTICLE; BURSAPHELENCHUS XYLOPHILUS; CAENORHABDITIS ELEGANS; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; EPIMERIZATION; FERMENTATION; GRIGNARD REACTION; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HYDROGENATION; NEMATOCIDAL ACTIVITY; NONHUMAN; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84925507467     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2015.02.038     Document Type: Article

References (37)

1. D.J. Newman, and G.M. Cragg J. Nat. Prod. 70 2007 461 477
2. D.J. Newman, and G.M. Cragg J. Nat. Prod. 75 2012 311 335
3. S. Omura Tetrahedron 67 2011 6420 6459
4. T. Nakashima, R. Okuyama, Y. Kamiya, A. Matsumoto, M. Iwatsuki, Y. Inahashi, K. Yamaji, Y. Takahashi, and S. Omura J. Antibiot. 6 2013 311 317
5. T. Nakashima, M. Iwatsuki, J. Ochiai, Y. Kamiya, K. Nagai, A. Matsumoto, A. Ishiyama, K. Otoguro, K. Shiomi, Y. Takahashi, and S. Omura J. Antibiot. 6 2013 253 260
6. T. Nakashima, Y. Kamiya, M. Iwatsuki, Y. Takahashi, and S. Omura J. Antibiot. 67 2014 533 539
7. S. Geerts, and B. Gryseels Clin. Microbiol. Rev. 13 2000 207 222
8. R.W. Burg, B.M. Miller, E.E. Baker, J. Birnbaum, S.A. Currie, R. Hartman, Y.L. Kong, R.L. Monaghan, G. Olson, I. Putter, J.B. Tunac, H. Wallick, E.O. Stapley, R. Oiwa, and S. Omura Antimicrob. Agents Chemother. 15 1979 361 367
9. A. Harder, H.P. Schmitt-Wrede, J. Krücken, P. Marinovski, F. Wunderlich, J. Willson, K. Amliwala, L. Holden-Dye, and R. Walker Int. J. Antimicrob. Agents 22 2003 318 331
10. L.B. Townsend, and D.S. Wise Parasitol. Today 6 1990 107 112
11. M.L. Aubry, P. Cowell, M.J. Davey, and S. Shevde Br. J. Pharmacol. 38 1970 332 344
12. G.A. EI-Shahawi, M. Abdel-Latif, A.H. Saad, and M. Bahgat Exp. Parasitol. 126 2010 603 610
13. S. Omura, K. Otoguro, N. Imamura, H. Kuga, Y. Takahashi, R. Masuma, Y. Tanaka, and H. Tanaka J. Antibiot. 40 1987 623 629
14. N. Imamura, H. Kuga, K. Otoguro, H. Tanaka, and S. Omura J. Antibiot. 42 1989 156 158
15. M. Yamato, H. Iinuma, H. Naganawa, Y. Yamagishi, M. Hamada, T. Masuda, and H. Umezawa J. Antibiot. 39 1986 184 191
16. M. Nakayama, Y. Takahashi, H. Itoh, K. Kamiya, M. Shiratsuchi, and G. Otani J. Antibiot. 42 1989 1535 1540
17. M. Fujiu, S. Sawairi, H. Shimada, H. Takaya, Y. Aoki, T. Okuda, and K. Yokose J. Antibiot. 47 1994 833 835
18. C.L. Stevens, B.T. Gillis, J.C. French, and T.H. Haskell J. Am. Chem. Soc. 78 1956 3229 3230
19. C.L. Stevens, B.T. Gillis, J.C. French, and T.H. Haskell J. Am. Chem. Soc. 80 1958 6088 6092
20. C.L. Stevens, B.T. Gillis, and T.H. Haskell J. Am. Chem. Soc. 81 1959 1435 1437
21. J. Swigert, and K.G. Taylor J. Am. Chem. Soc. 93 1971 7337 7338
22. K.G. Taylor, and T. Riehl J. Am. Chem. Soc. 94 1972 250 255
23. W. Giencke, O. Ort, and H. Stark Liebigs Ann. Chem. 7 1989 671 676
24. K. Tsuzuki, F.-S. Yan, K. Otoguro, and S. Omura J. Antibiot. 44 1991 774 784
25. R.A. Moss, and M. Matsuo J. Am. Chem. Soc. 99 1977 1643 1645
26. R.A. Moss J. Org. Chem. 31 1966 1082 1087
27. R.A. Moss, and M.J. Landon Tetrahedron Lett. 10 1969 3897 3900
28. R.A. Moss, M.J. Landon, K.M. Luchter, and A. Mamantov J. Am. Chem. Soc. 94 1972 4392 4394
29. R.A. Moss, and G.M. Love Tetrahedron Lett. 14 1973 4701 4704
30. Y. Takahashi, H. Ishiwata, T. Deushi, M. Nakayama, and M. Shiratsuchi Tetrahedron Lett. 32 1991 1067 1068
31. M. Nakata, S. Kawazoe, T. Tamai, K. Tatsuta, H. Ishiwata, Y. Takahashi, Y. Okuno, and T. Deushi Tetrahedron Lett. 34 1993 6095 6098
32. M.J. Gorczynski, J. Huang, and S.B. King Org. Lett. 8 2006 2305 2308
33. P. Cerea, C. Giannini, D. Dall'Angelo, E. Licandro, S. Maiorana, and R. Marchelli Tetrahedron 63 2007 4108 4119
34. J.S. Dickschat, H. Bruns, and R. Riclea Beilstein J. Org. Chem. 7 2011 1697 1712
35. A. Krasovskiy, F. Kopp, and P. Knochel Angew. Chem., Int. Ed. 45 2006 497 500
36. T. Kitahara, S. Aono, and K. Mori Biosci. Biotechnol. Biochem. 59 1995 78 82
37. M. Kusano, H. Koshino, J. Uzawa, S. Fujioka, T. Kawano, and Y. Kimura Biosci. Biotechnol. Biochem. 64 2000 2559 2568