Synthesis of phenol abietane diterpenes based on the oxidative radical cyclization utilizing the Mn(OAc)3/Ac2O system

Synlett

Volumn , Issue 15, 2007, Pages 2425-2429

  Alvarez Manzaneda, Enrique ^a   Chahboun, Rachid ^a   Cabrera, Eduardo ^a   Alvarez, Esteban ^a   Alvarez Manzaneda, Ramón ^b   Lachkar, Mohammed ^c   Messouri, Ibtissam ^c  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF ALMERÍA   (Spain)

^c MOHAMMED V UNIVERSITY   (Morocco)

Author keywords

Abietane diterpenoids; Enantiospecific synthesis; Phenols

Indexed keywords

19 HYDROXYFERRUGINOL; ABIETANE DERIVATIVE; ACETIC ANHYDRIDE; ACETYLSALICYLIC ACID; BETA OXOCARBOXYLIC ACID ESTER; ESTER DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; MANGANESE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; SYNTHESIS;

EID: 34948815024     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-985586     Document Type: Article

References (44)

1. For some references on the biological activities, see: (a) Nakatani, N.; Iwatani, R. Agric. Biol. Chem. 1984, 48, 2081.
2. (b) Achenbach, H.; Walbel, R.; Nkunya, M. H. H.; Weenen, H. Phytochemistry 1992, 31, 3781.
3. (c) Moujir, L.; Gutierrez-Navarro, A. M.; San Andrés, L.; Luis, J. G. Phytochemistry 1993, 34, 1493.
4. (d) Ulubelen, A.; Topcu, G.; Eris, C.; Sonmez, U.; Kartal, M.; Kurucu, S.; Bozok-Johansson, C. Phytochemistry 1994, 36, 971.
5. (e) Tada, M.; Chiba, K.; Okuno, K.; Ohnishi, E.; Yoshii, T. Phytochemistry 1994, 35, 539.
6. (f) Batista, O.; Simoes, M. F.; Duarte, A.; Valdivia, M. L.; De La Torre, M. C.; Rodriguez, B. Phytochemistry 1995, 38, 167.
7. (g) Dellar, J. E.; Cole, M. D.; Waterman, P. G. Phytochemistry 1996, 41, 735.
8. (h) Ulubelen, A.; Sonmez, U.; Topcu, G.; Bozok-Johansson, C. Phytochemistry 1996, 42, 145.
9. (i) Gao, J.; Han, G. Phytochemistry 1997, 44, 759.
10. (j) Marrero, J. G.; Andres, L. S.; Luis, J. G. J. Nat. Prod. 2002, 65, 986.
11. Tan, N.; Kaloga, M.; Radtke, O. A.; Kiderlen, A. F.; Oksuz, S.; Ulubelen, A.; Kolodziej, H. Phytochemistry 2002, 61, 881.
12. (a) Alvarez-Manzaneda, E. J.; Chahboun, R.; Bentaleb, F.; Cabrera Torres, E.; Alvarez, E.; Haidour, A.; Ramos López, J. M.; Alvarez-Manzaneda, R.; El Houssame, S. Synlett 2004, 2701.
13. (b) Matsushita, Y.; Iwakiri, Y.; Yoshida, S.; Sugamoto, K.; Matsui, T. Tetrahedron Lett. 2005, 46, 3629.
14. (c) Yajima, A.; Yamaguchi, A.; Saitou, F.; Nukada, T.; Yabuta, G. Tetrahedron 2007, 63, 1080.
15. Kofujita, H.; Ota, M.; Taakahashi, K.; Kawai, Y.; Hayashi, Y. Phytochemistry 2002, 61, 895.
16. (a) Kupchan, S. M.; Karim, A.; Marcks, C. J. Org. Chem. 1969, 34, 3912.
17. (b) Kupchan, S. M.; Karim, A.; Marcks, C. J. Am. Chem. Soc. 1968, 90, 5924.
18. Haslinger, E.; Michl, G. Tetrahedron Lett. 1988, 29, 5751.
19. (a) Gil, R. R.; Cordell, G. A. J. Nat. Prod. 1994, 57, 181.
20. (b) Lin, L. Z.; Blasko, G.; Cordell, G. A. Phytochemistry 1989, 28, 177.
21. Arihara, S.; Umeyama, A.; Bando, S.; Imoto, S.; Ono, M.; Tani, M.; Yoshikawa, K. Chem. Pharm. Bull. 2004, 52, 354.
22. Cambie, R. C.; Cox, R. E.; Sidwell, D. Phytochemistry 1984, 23, 333.
23. Takei, M.; Umeyama, A.; Arihara, S. Biochem. Biophys. Res. Commun. 2005, 337, 730.
24. Hairing, S. R.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 1499.
25. (a) Engler, T. A.; Sampath, U.; Naganathan, S.; Vander Velde, D.; Takusagawa, F. J Org. Chem. 1989, 54, 5712.
26. (b) Zambrano, J. L.; Rosales, V.; Nakano, T. Tetrahedron Lett. 2003, 44, 1859.
27. (a) Banik, B. K.; Ghosh, S.; Ghatak, V. R. Tetrahedron 1988, 44, 6947.
28. (b) Majetich, G.; Siesel, D. Synlett 1995, 559.
29. (c) Majetich, G.; Liu, S.; Fang, J.; Siesel, D.; Zhang, Y. J. Org. Chem. 1997, 62, 6928.
30. (d) Tada, M.; Nishiiri, S.; Zhixiang, Y.; Imai, Y.; Tajima, S.; Okazaki, N.; Kitano, Y.; Chiba, K. J. Chem. Soc., Perkin Trans. 1 2000, 2657.
31. Shishido, K.; Got, K.; Miyoshi, S.; Takaishi, Y.; Shibuya, M. J. Org. Chem. 1994, 59, 406.
32. Bhar, S. S.; Ramana, M. M. V. J. Org. Chem. 2004, 69, 8935.
33. Bendell, J. G.; Cambie, R. C.; Rutledge, P. S.; Woodgate, P. D. Aust. J. Chem. 1993, 46, 1825.
34. (a) Tahara, A.; Akita, H. Chem. Pharm. Bull. 1975, 23, 197.
35. (b) Gigante, B.; Santos, C.; Silva, A. M.; Curto, M. J. M.; Nascimento, M. S. J.; Pinto, E.; Pedro, M.; Cerqueira, F.; Pinto, M. M.; Duarte, M. P.; Laires, A.; Rueff, J.; Gonçalves, J.; Pegado, M. I.; Valdeira, M. L. Bioorg. Med. Chem. 2003, 11, 1631.
36. (a) Alvarez-Manzaneda, E.; Chahboun, R.; Guardia, J. J.; Lachkar, M.; Dahdouh, A.; Lara, A.; Messouri, I. Tetrahedron Lett. 2006, 47, 2577.
37. (b) Alvarez-Manzaneda, E.; Chahboun, R.; Cabrera, E.; Alvarez, E.; Alvarez-Manzaneda, R.; Lachkar, M.; Messouri, I. Tetrahedron Lett. 2007, 48, 989.
38. Pascual Teresa, J. de; San Feliciano, A.; Miguel del Corral, J. M.; Barrero, A. F. Phytochemistry 1983, 22, 300.
39. Ahond, A.; Carnero, P.; Gastambide, B. Bull. Soc. Chim. Fr. 1964, 348.
40. The epoxidation of ester 18 to give compounds 19 and 20 was previously described by Barrero et al., who reported a 40% yield for this transformation. See: Barrero, A. F.; Quintana, R.; Altarejos, J. Tetrahedron 1991, 47, 4441.
41. Aldehyde 16 was obtained by the same procedure from the mixture of 12R,13S- and 12S, 13R-epoxy derivatives, resulting from the epoxidation of methyl cis-communate. See: Barrero, A. F.; Sánchez, J. F.; Elmerabet, J.; Jimenez-Gonzalez, D.; Macías, F. A.; Simonet, A. M. Tetrahedron 1999, 55, 7289.
42. Snider, B. B.; Patricia, J. J. J. Org. Chem. 1989, 54, 38.
43. 2O (10 x 30 mL) and brine (3 x 20 mL). The dried organic layer was evaporated and the residue was directly purified by flash chromatography (hexane-t-BuOMe, 7:3) to yield 22 (0.82 g, 74%) as a yellow syrup.
44. Spectroscopic properties of natural terpenoids (10 and 11) were identical to those reported in the literature. All new compounds were fully characterized spectroscopically and had satisfactory high-resolution mass spectroscopy data.