Structural reassignment of a marine metabolite from a binaphthalenetetrol to a tetrabrominated diphenyl ether

Journal of Natural Products

Volumn 75, Issue 6, 2012, Pages 1125-1129

  Podlesny, Erin E ^a   Kozlowski, Marisa C ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIBROMO 2 (3,5 DIBROMO 2 METHOXYPHENOXY)PHENOL; BINAPHTHALENETETROL; DIPHENYL ETHER DERIVATIVE; DRUG METABOLITE; NAPHTHALENE DERIVATIVE; NATURAL PRODUCT; QUINONE DERIVATIVE; UNCLASSIFIED DRUG; 3,5-DIBROMO-2-(3,5-DIBROMO-2-METHOXYPHENOXY)PHENOL; BIOLOGICAL PRODUCT;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; X RAY CRYSTALLOGRAPHY; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; MARINE BIOLOGY; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

BIOLOGICAL AGENTS; CRYSTALLOGRAPHY, X-RAY; HALOGENATED DIPHENYL ETHERS; MARINE BIOLOGY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM;

EID: 84866440218     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np300141t     Document Type: Article

References (22)

1. Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc. Rev. 2009, 38, 3193-3207.
2. (a) DiVirgilio, E. S.; Dugan, E. C.; Mulroony, C. A.; Kozlowski, M. C. Org. Lett. 2007, 9, 385-388.
3. (b) Kozlowski, M. C.; Dugan, E. C.; DiVirgilio, E. S.; Maksimenka, K.; Bringmann, G. Adv. Synth. Catal. 2007, 349, 583-594.
4. (a) Morgan, B. J.; Dey, S.; Johnson, S. W.; Kozlowski, M. C. J. Am. Chem. Soc. 2009, 131, 9413-9425.
5. (b) Morgan, B. J.; Mulrooney, C. A.; Kozlowski, M. C. J. Org. Chem. 2010, 75, 44-56.
6. (a) O'Brien, E. M.; Morgan, B. J.; Kozlowski, M. C. Angew. Chem., Int. Ed. 2008, 47, 6877-6880.
7. (b) O'Brien, E. M.; Morgan, B. J.; Mulrooney, C. A.; Kozlowski, M. C. J. Org. Chem. 2010, 75, 57-68.
8. (a) Mulrooney, C. A.; Morgan, B. J.; Li, X.; Kozlowski, M. C. J. Org. Chem. 2010, 75, 16-29.
9. (b) Morgan, B. J.; Mulrooney, C. A.; O'Brien, E. M.; Kozlowski, M. C. J. Org. Chem. 2010, 75, 30-43.
10. (c) O'Brien, E. M.; Li, J.; Carroll, P. J.; Kozlowski, M. C. J. Org. Chem. 2010, 75, 69-73.
11. Podlesny, E. E.; Kozlowski, M. C. Org. Lett. 2012, 14, 1408-1411.
12. Dai, J.; Liu, Y.; Zhou, Y.-D.; Nagle, D. G. J. Nat. Prod. 2007, 70, 1824-1826.
13. (a) Somei, H.; Asano, Y.; Yoshida, T.; Takizawa, S.; Yamataka, H.; Sasai, H. Tetrahedron Lett. 2004, 45, 1841-1844.
14. (b) Guo, Q.-X.; Wu, Z.-J.; Luo, Z.-B.; Liu, Q.-Z.; Ye, J.-L.; Luo, S.-W.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2007, 129, 13927-13938.
15. (c) Takizawa, S.; Katayama, T.; Sasai, H. Chem. Commun. 2008, 4113-4122.
16. (d) Takizawa, S.; Katayama, T.; Somei, H.; Asano, Y.; Yoshida, T.; Kameyama, C.; Rajesh, D.; Onitsuka, K.; Suzuki, T.; Mikami, M.; Yamataka, H.; Jayaprakash, D.; Sasai, H. Tetrahedron 2008, 64, 3361-3371.
17. (e) Takizawa, S.; Katayama, T.; Kameyama, C.; Onitsuka, K.; Suzuki, T.; Yanagida, T.; Kawai, T.; Sasai, H. Chem. Commun. 2008, 1810-1812.
18. Copies of the original 1H and 13C NMR spectra and a sample of the natural product isolate were kindly provided by Dr. Nagle (see ref 7).
19. Norton, R. S.; Croft, K. D.; Wells, R. J. Tetrahedron 1981, 37, 2341-2349.
20. Hattori, T.; Konno, A.; Adachi, K.; Shizuri, Y. Fisheries Sci. 2001, 67, 899-903.
21. Observed 1H and 13C NMR chemical shifts appear to be concentration dependent.
22. Compound 8 was reported from the sponge Phyllospongia dendyi. This sponge has been taxonomically reclassified as Lendenfeldia dendyi: Bergquist, P. R. New Zeal. J. Zool. 1980, 7, 443-503.