Tripartilactam, a cyclobutane-bearing tricyclic lactam from a Streptomyces sp. in a dung beetle's brood ball

Organic Letters

Volumn 14, Issue 5, 2012, Pages 1258-1261

  Park, Seon Hui ^a   Moon, Kyuho ^a   Bang, Hea Son ^b   Kim, Seong Hwan ^a   Kim, Dong Gyu ^a   Oh, Ki Bong ^c   Shin, Jongheon ^a   Oh, Dong Chan ^a  

^a Seoul National University   (South Korea)

^b National Academy of Agricultural Science   (South Korea)

^c Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; LACTAM; LOOP DIURETIC AGENT; TRIPARTILACTAM;

ANIMAL; ARTICLE; BEETLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; FECES; HUMAN; ISOLATION AND PURIFICATION; MICROBIOLOGY; STREPTOMYCES; TUMOR CELL LINE;

ANIMALS; BEETLES; CELL LINE, TUMOR; CELL SURVIVAL; CYCLOBUTANES; FECES; HUMANS; LACTAMS; MOLECULAR STRUCTURE; SODIUM POTASSIUM CHLORIDE SYMPORTER INHIBITORS; STREPTOMYCES;

EID: 84863230340     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300108z     Document Type: Article

References (21)

1. Crawford, J. M.; Clardy, J. Chem. Commun. 2011, 47, 7559
2. Bode, H. B. Angew. Chem., Int. Ed. 2009, 48, 6394
3. Kaltenpoth, M. Trends Microbiol. 2009, 17, 529
4. Scott, J. J.; Oh, D.-C.; Yuceer, M. C.; Klepzig, K. D.; Clardy, J.; Currie, C. R. Science 2008, 322, 63
5. Oh, D.-C.; Scott, J. J.; Currie, C. R.; Clardy, J. Org. Lett. 2009, 11, 633
6. Oh, D.-C.; Poulsen, M.; Currie, C. R.; Clardy, J. Nat. Chem. Biol. 2009, 5, 391
7. Oh, D.-C.; Poulsen, M.; Currie, C. R.; Clardy, J. Org. Lett. 2011, 13, 752
8. Poulsen, M.; Oh, D.-C.; Clardy, J.; Currie, C. R. PLoS One 2011, 6, e16763
9. Zhang, Y. L.; Ge, H. M.; Zhao, W.; Dong, H.; Xu, Q.; Li, S. H.; Li, J.; Zhang, J.; Song, Y. C.; Tan, R. X. Angew. Chem., Int. Ed. 2008, 47, 5823
10. Freinkman, E.; Oh, D.-C.; Scott, J. J.; Currie, C. R.; Clardy, J. Tetrahedron Lett. 2009, 50, 6834
11. Fincher, G. T. J. Ga. Entomol. Soc. 1981, 16, 316
12. Kim, S.-H.; Ko, H.; Bang, H.-S.; Park, S.-H.; Kim, D.-G.; Kwon, H. C.; Kim, S. Y.; Shin, J.; Oh, D.-C. Bioorg. Med. Chem. Lett. 2011, 21, 5715
13. Pretsch, E.; Bühlmann, P.; Affolter, C. Structure Determination of Organic Compounds-Tables of Spectral Data; Springer: New York, 2000; p 176.
14. Yabuuchi, T.; Kusumi, T. J. Org. Chem. 2000, 65, 397
15. Seco, J. M.; Quiñoá, E.; Riguera, R. Tetrahedron: Asymmetry 2001, 12, 2915
16. Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: 1991; p 322. For another possible cyclobutane formation mechanism by unusual oxidative cyclization or radical cascading proposed in the ladderane biosynthesis, see
17. Rattary, J. E.; Strous, M.; Op den Camp, H. J. M.; Schouten, S.; Jetten, M. S. M.; Damsté, J. S. S. Biol. Direct 2009, 4, 8
18. Jacobsson, U.; Kumar, V.; Saminathan, S. Phytochemistry 1995, 39, 839
19. Macleod, J. K.; Rasmussen, H. B. Phytochemistry 1999, 50, 105
20. Sung, P.-J.; Chuang, L.-F.; Kuo, J.; Chen, J.-J.; Fan, T.-Y.; Li, J.-J.; Fang, L.-S. Chem. Pharm. Bull. 2007, 55, 1296
21. Groweiss, A.; Kashman, Y. Tetrahedron 1983, 39, 3385