Total synthesis of an oxepine natural product, (±)-janoxepin

Organic Letters

Volumn 14, Issue 4, 2012, Pages 1122-1125

  Doveston, Richard G ^a   Steendam, René ^a   Jones, Stuart ^a   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PRODUCT; JANOXEPIN; PIPERAZINE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

ARTICLE; ASPERGILLUS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ASPERGILLUS; BIOLOGICAL AGENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERAZINES; PYRIMIDINONES;

EID: 84857200734     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300039x     Document Type: Article

References (23)

1. Sprogøe, K.; Manniche, S.; Larsen, T. O.; Christopherson, C. Tetrahedron 2005, 61, 8718
2. Yamaguchi, S. Heterocycles 2009, 79, 243
3. Snyder, N. L.; Haines, H. M.; Peczuh, M. W. Tetrahedron 2006, 62, 9301
4. Elliott, M. C. J. Chem. Soc., Perkin Trans. 1 2002, 2301
5. Codelli, J. A.; Puchlopek, A. L. A.; Reisman, S. E. J. Am. Chem. Soc., DOI: 10.1021/ja209354e, Publication Date (Web): 24 Oct 2011.
6. For naturally occurring dibenzo-oxepines and their synthesis, see: Olivera, R.; San Martin, R.; Churruca, F.; Dominguez, E. Org. Prep. Proced. Int. 2004, 36, 297
7. Cutler, H. G.; Springer, J. P.; Arrendale, R. F.; Arison, B. H.; Cole, P. D.; Roberts, R. G. Agric. Biol. Chem. 1988, 52, 1725
8. Belofsky, G. N.; Anguera, M.; Jenson, P. R.; Fenical, W.; Köck, M. Chem.-Eur. J. 2000, 6, 1355
9. Lu, X.-H.; Shi, Q.-W.; Zheng, Z.-H.; Ke, A.-B.; Zhang, H.; Huo, Y.; Ma, C.-H.; Ren, X.; Li, Y.-Y.; Lin, J.; Jiang, Q.; Gu, Y.-C.; Kiyota, H. Eur. J. Org. Chem. 2011, 4, 802
10. Li, G.-Y.; Li, L.-M.; Yang, T.; Chen, X.-Z.; Fang, D.-M.; Zhang, G.-L. Helv. Chim. Acta 2010, 93, 2075
11. Lee, S. U.; Asami, Y.; Lee, D.; Jang, J.-H.; Ahn, J. S.; Oh, H. J. Nat. Prod 2011, 74, 1284
12. Ookura, R.; Kito, K.; Ooi, T.; Namikoshi, M.; Kusumi, T. J. Org. Chem. 2008, 73, 4245
13. See also (erroneous structural assignment): Rahbæck, L.; Breinholt, J.; Frisvad, J. C.; Christopherson, C. J. Org. Chem. 1999, 64, 1689
14. Bode, H. B.; Bethe, B.; Höfs, R.; Zeeck, A. ChemBioChem 2002, 3, 619
15. Frizler, M.; Lohr, F.; Furtmann, N.; Kläs, J.; Gütschow, M. J. Med. Chem. 2011, 54, 396
16. Kuse, M.; Kondo, N.; Ohyabu, Y.; Isobe, M. Tetrahedron 2004, 60, 835
17. Ramachary, D. B.; Ramakumar, K.; Bharanishashank, A.; Narayana, V. V. J. Comb. Chem. 2010, 12, 855 and references therein
18. Dura, R. D.; Paquette, L. A. Synthesis 2006, 2837
19. Boyd, D. R.; O'Kane, G. A. Tetrahedron Lett. 1987, 38, 6395
20. Agarwal, R.; Boyd, D. R. J. Chem. Soc., Perkin Trans. 1 1993, 2869
21. Hoffmann, H.; Djafara, H. Z. Naturforsch. 1989, 44b, 220
22. CCDC 848130 (1) contains the supplementary crystallographic data for this compound. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data-request/cif.
23. Martin, J.; Plaquevent, J. C.; Maddaluno, J.; Rouden, J.; Lasne, M. C. Eur. J. Org. Chem. 2009, 5414 and references therein