Photosensitized conversion of 9,10-deoxytridachione to photodeoxytridachione

Organic Letters

Volumn 7, Issue 22, 2005, Pages 4959-4962

  Zuidema, Daniel R ^a   Miller, Aubry K ^b   Trauner, Dirk ^b   Jones, Paul B ^a  

^a WAKE FOREST UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 PENTADIENE; 1,3-PENTADIENE; 1,4 CYCLOHEXADIENE; 1,4-CYCLOHEXADIENE; 9,10 DEOXYTRIDACHIONE; 9,10-DEOXYTRIDACHIONE; ALKADIENE; CYCLOHEXANE DERIVATIVE; CYCLOHEXENE DERIVATIVE; PENTANE; PROPIONIC ACID DERIVATIVE; PYRONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; LIGHT; PHOTOCHEMISTRY; RADIATION EXPOSURE;

ALKADIENES; CYCLOHEXANES; CYCLOHEXENES; LIGHT; MOLECULAR STRUCTURE; PENTANES; PHOTOCHEMISTRY; PROPIONATES; PYRONES;

EID: 27644440832     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051887c     Document Type: Article

References (35)

1. (a) Cimino, G.; Ciavatta, M. L.; Fontana, A.; Gavagnin, M. In Bioactive Compounds from Natural Sources; Corrado Tringali, Ed.; Taylor and Francis: London, 2001; Chapter 15, pp 577-637.
2. (b) Di Marzo, V.; Vardaro, R. R.; De Petrocellis, L.; Villani, G.; Minei, R.; Cimino, G. Experientia 1991, 47, 1221-1227.
3. (c) Gavagnin, M.; Mollo, E.; Cimino, G.; Ortea, J. Tetrahedron Lett. 1996, 37, 4259-4262.
4. (d) Ksebati, M. B.; Schmitz, F. J. J. Org. Chem. 1985, 50, 5637-5642.
5. (e) Gavagnin, M.; Spinella, A.; Castelluccio, F.; Cimino, G. J. Nat. Prod. 1994, 57, 298-304.
6. (a) Marin, A.; Ros, J. Sci. Mar. 2004, 68 Supp. 1, 227-241.
7. (b) Gavagnin, M.; Mollo, E.; Montanaro, D.; Ortea, J.; Cimino, G. J. Chem. Ecol. 2000, 26, 1563-1578.
8. (c) Cimino, G.; Fontana, A.; Gavagnin, M. Curr. Org. Chem. 1999, 3, 327-372.
9. (d) Gavagnin, M.; Marin, A.; Mollo, E.; Crispino, A.; Villani, G.; Cimino, G. Comp. Biochem. Physiol., B 1994, 108, 107-115.
10. (a) Ireland, C.; Faulkner, J. Tetrahedron 1981, 37 Suppl. 1, 233-240.
11. (b) Ireland, C.; Scheuer, P. J. Science 1979, 205, 922-923.
12. Miller, A. K.; Trauner, D. Angew. Chem., Int. Ed. 2003, 42, 549-552.
13. (a) Moses, J. E.; Adlington, R. M.; Rodriguez, R.; Eade, S. J.; Baldwin, J. E. Chem. Commun. 2005, 1687-1689.
14. (b) Miller, A. K.; Trauner, D. Angew. Chem., Int. Ed. 2005, 44, 4602-4606.
15. (a) Moses, J.; Baldwin, J. E.; Bruckner, S.; Eade, S. J.; Adlington, R. M. Org. Biomol. Chem. 2003, 1, 3670-3684.
16. (b) Bruckner, S.; Baldwin, J. E.; Moses, J.; Adlington, R. M.; Cowley, A. Tetrahedron Lett. 2003, 44, 7471-7473.
17. (a) Ciavatta, M. L.; Trivellone, E.; Villani, G.; Cimino, G. Tetrahedron Lett. 1993, 34, 6791-6794.
18. (b) Vardaro, R. R.; Di Marzo, V.; Crispino, A.; Cimino, G. Tetrahedron 1991, 47, 5569-5576.
19. (c) Vardaro, R. R.; Di Marzo, V. D.; Cimino, G. Tetrahedron Lett. 1992, 33, 2875-2878.
20. (d) Cutignano, A.; Fontana, A.; Renzulli, L.; Cimino, G. J. Nat. Prod. 2003, 66, 1399-1401.
21. Zuidema, D. R.; Jones, P. B. J. Nat. Prod. 2005, 68, 481-486.
22. Murov, S. L.; Carmichael, I.; Hug, G. L. Triplet State Energies: Ordered. In Handbook of Photochemistry, 2nd ed.; Dekker: New York, 1993; pp 54-98.
23. Fu, X.; Hong, E. P.; Schmitz, F. J. Tetrahedron 2000, 56, 8989-8993.
24. (a) Cueto, M.; D'Croz, L.; Mate, J. L.; San-Martin, A.; Darias, J. Org. Lett. 2005, 7, 415.
25. (b) Barbarow, J. E.; Miller, A. K.; Trauner, D. Org. Lett. 2005, 7, 2901-2903.
26. (a) Dauben, W. G.; Kellogg, M. S. J. Am. Chem. Soc. 1972, 94, 8951-8953.
27. (b) Dauben, W. G.; Smith, J. H. J. Org. Chem. 1967, 32, 3244-3246.
28. (c) Evanega, G. R.; Bergmann, W.; English, J., Jr. J. Org. Chem. 1962, 27, 13-20.
29. (d) Dauben, W. G. Pure Appl. Chem. 1973, 33, 197-215.
30. (a) Turro, N. J. Theoretical Organic Photochemistry. In Modern Molecular Photochemistry, 2nd ed.; University Science Books: Mill Valley, CA, 1991; pp 199-231.
31. (b) Giese, B.; Wettstein, P.; Stahelin, C.; Barbosa, F.; Neuberger, M.; Zehnder, M.; Wessig, P. Angew. Chem., Int. Ed. 1999, 38, 2586.
32. (c) Bartlett, P. D.; Porter, N. A. J. Am. Chem. Soc. 1968, 90, 5317.
33. Zimmerman, H. E.; Epling, G. J. Am. Chem. Soc. 1972, 94, 8749-8761.
34. Engel, P. S.; Monroe, B. C. Adv. Photochem. 1971, 8, 245-313.
35. Yoshida, Z.; Takabayashi, F. Tetrahedron 1968, 24, 933-943.