Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure

Organic and Biomolecular Chemistry

Volumn 3, Issue 15, 2005, Pages 2868-2871

  Protti, Stefano ^a   Fagnoni, Maurizio ^a   Albini, Angelo ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; DNA; IRRADIATION; PHENOLS; POSITIVE IONS; SALTS; SOLVENTS; SYNTHESIS (CHEMICAL);

BIOACTIVE ALLYPHENOLS; CATION INTERMEDIATES; POLAR SOLVENTS;

GENES;

METAL; PHENOL DERIVATIVE;

ARTICLE; CHEMISTRY; PHOTOCHEMISTRY; PIPERACEAE;

METALS; PHENOLS; PHOTOCHEMISTRY; PIPER;

PIPERACEAE;

EID: 23844493508     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b506735a     Document Type: Article

References (47)

1. V. S. Parmar, S. C. Jain, K. P. Bisht, R. Jain, P. Taneja, A. Jha, O. D. Tyagi, A. K. Prasad, J. Wengel, C. E. Olsen and P. M. Boll, Phytochemislry, 1997, 46, 597.
2. T.-Y. Liu, Y.-T. Chung, P.-F. Wang, C.-W. Chi and L.-L. Hsieh, Mutat. Res., 2004, 559, 59.
3. P. H. Espeel, B. Janssens and P. A. Jacobs, J. Org. Chem., 1993, 58, 7688;
4. I. Shimizu, T. Sakamoto, S. Kawaragi, Y. Maruyama and A. Yamamoto, Chem. Lett., 1997, 137.
5. (a) A. Inoue, K. Kitagawa, H. Shinokubo and K. Oshima, J. Org. Chem., 2001, 66, 4333;
6. (b) Y. Kondo, N. Takazawa, C. Yamazaki and T. Sakamoto, J. Org. Chem., 1994, 59, 4717;
7. (c) E. Wenkert, J. B. Fernandes, E. L. Michelotti and C. S. Swindell, Synthesis, 1983, 701;
8. (d) P. Gomes, C. Gosmini and J. Périchon, Org. Lett., 2003, 5, 1043;
9. (e) A. F. Littke and G. C. Fu, Angew. Chem., Int. Ed., 1999, 38, 2411;
10. (f) D. Bouyssi, V. Gerusz and G. Balme, Eur. J. Org. Chem., 2002, 2445.
11. (a) W. Gu, X. She, X. Pan and T.-K. Yang, Tetrahedron: Asymmetry, 1998. 9, 1377;
12. (b) H. Saimoto, J. Ueda, H. Sashiwa, Y. Shigemasa and T. Hiyama, Bull. Chem. Soc. Jpn., 1994, 67, 1178.
13. (a) S. Protti, M. Fagnoni, M. Mella and A. Albini, J. Org. Chem., 2004, 69, 3465;
14. (b) B. Guizzardi, M. Mella, M. Fagnoni and A. Albini, Chem. Eur. J, 2003, 9, 1549.
15. M. Mella, P. Coppo, B. Guizzardi, M. Fagnoni, M. Freccero and A. Albini, J. Org. Chem., 2001, 66, 6344;
16. S. Milanesi, M. Fagnoni and A. Albini, J. Org. Chem., 2005, 70, 603.
17. J. Tuyet, Tetrahedron Lett., 2000, 41, 8445.
18. Estragole can also be obtained in nearly quantitative yields from irradiation of p-methoxyphenylmesylate or Inflate in the presence of ATMS. See: M. De Carolis, S. Protti, M. Fagnoni and A. Albini, Angew. Chem., Int. Ed., 2005, 44, 1232.
19. Diazonium salts have been demonstrated to be suitable precursors of triplet phenyl cation when appropriate triplet sensitizers (e.g. xanthone) are used, because direct irradiation may lead to singlet rather than triplet aryl cations. The singlet cation add to the solvent. See: S. Milanesi, M. Fagnoni and A. Albini, Chem. Commun., 2003, 216.
20. A protic medium was a must in the case of fluorinated 1b, similar to that which was observed in the case of 4-fluoroaniline, where the photoheterolytic path is exothermic only thanks to the formation of the H-F bond. See: M. Freccero, M. Fagnoni and A. Albini, J. Am. Chem. Soc., 2003, 125, 13182.
21. B. Guizzardi, M. Mella, M. Fagnoni and A. Albini, J. Org. Chem., 2003, 68, 1067.
22. H. Mayr, B. Kempf and A. R. Ofial, Acc. Chem. Res., 2003, 36, 66.
23. Indeed, the less nucleophilic benzene (N < -4.47) did not trap the 4-methoxyphenyl cation in MeCN or AcOEt, while with 2,3-dimethyl-2-butene (N = -1.0) arylation occurred efficiently (ca. 70% yield),see ref. 6a.
24. For a recent reviews on allylsilane chemistry, see: L. Chabaud, P. James and Y. Landais, Eur. J. Org. Chem., 2004, 3173.
25. K. Omura and T. Matsuura, Synthesis, 1971, 28.
26. D. Mangion and D. R. Arnold, Can. J. Chem., 1999, 77, 1655.
27. Examples of this radicalic fragmentation have been reported, see: M. A. Miranda and F. Galindo, Photo-Fries reaction and related processes, in CRC Handbook of Organic Photochemistry and Photobiology, ed. W. Horspool and F. Lenci, CRC Press, Boca Raton, 2nd edn., 2004, p. 42-1.
28. (a) J. Den Heijer, O. B. Shadid, J. Cornelisse and E. Havinga, Tetrahedron, 1977, 33, 779;
29. (b) S. Caron, E. Vazquez and J. M. Wojcik, J. Am. Chem. Soc., 2000, 122, 712;
30. (c) V. P. W. Boehm, C. W. K. Gstoettmayr, T. Weskamp and W. A. Herrmann, Angew. Chem., Int. Ed., 2001, 40, 3387.
31. D. A. Widdowson and R. Wilhelm, Chem. Commun., 2003, 578;
32. Y. Mi Kim and S. Yu, J. Am. Chem. Soc., 2003, 125, 1696.
33. S. Gasper, C. Devadoss and G. B. Schuster, J. Am. Chem. Soc., 1995, 117, 5206.
34. H. Sato, T. Dan, E. Onuma, H. Tanaka, B. Aoki and H. Koga, Chem. Pharm. Bull., 1992, 40, 109.
35. F. Barrero, E. J. Alvarez-Manzanera and R. Chahbhoun, Tetrahedron, 1998, 54, 5635.
36. (a) G. Wenxin, S. Xuengong, P. Xinfu and Y. Teng-Kuei, Tetrahedron: Asymmetry, 1998, 9, 1377;
37. (b) A. P. H. J. Schenning, J.-D. Arndt, M. Ito, A. Stoddart, M. Schreiber, P. Siemsen, R. E. Martin, C. Boudon, J. P. Gisselbrecht, M. Gross, F. F. Volker and F. Diederich, Helv. Chim. Acta, 2001, 84, 296.
38. M. R. Agharahimi and N. A. LeBel, J. Org. Chem., 1995, 60, 1856.
39. A. Ozanne, L. Pouysegu, D. Depernet, B. Francois and S. Quideau, Org. Lett., 2003, 5, 2903.
40. M. Miyazawa and M. Hisama, J. Agric. Food Chem., 2001, 49, 4019.
41. R. A. Momin, R. S. Ramsewak and R. G. Nair, J. Agric. Food Chem., 2000, 48, 3785.
42. S. Datta, C.-L. Chang, K.-L. Yeh and R.-S. Liu, J. Am. Chem. Soc., 2003, 125, 9294.
43. T. Msuda, Y. Inazumi, Y. Yasumasa, W. Padolina, H. Kikuzaki and N. Nakatami, Phytochemistry, 1991, 30, 3227.
44. L. Barata, P. Baker and E. Ruveda, Phytochemistry, 1978, 17, 783.
45. J. Hyoetylaeinen, J. Knuutinen and E. Vilen, Chemosphere, 1995, 30, 891.
46. S. Higashiya, J. Fluorine Chem., 1999, 99, 189.
47. G. Bartoli, M. Bosco, R. Dalpozzo, E. Marcantoni, M. Massaccesi, S. Rinaldi and L. Sambri, Synlett, 2003, 39.