Straightforward synthesis of aromatic polycyclic terpenoids through biomimetic cascade cyclizations triggered by photochemical electron transfer

European Journal of Organic Chemistry

Volumn , Issue 8, 2004, Pages 1798-1802

  Rosales, Viale ^a   Zambrano, Jorge ^b   Demuth, Martin ^a  

^a MAX PLANCK INSTITUTE FOR CHEMICAL ENERGY CONVERSION   (Germany)

^b UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

Biomimetic cascade cyclizations; Biomimetic synthesis; Natural products; Photochemical electron transfer; Terpenoids

Indexed keywords

1,1,4A TRIMETHYL 1,2,3,4,4A,9,10,10A OCTAHYDROPHENANTHREN 2BETA OL; 1,1,4A,6 TETRAMETHYL 1,2,3,4,4A,9,10,10A OCTAHYDROPHENANTHREN 2BETA OL; 6 ISOPROPYL 1,1,4A TRIMETHYL 1,2,3,4,4A,9,10,10A OCTAHYDROPHENANTHREN 2BETA OL; ALCOHOL DERIVATIVE; AROMATIC COMPOUND; PHENANTHRENE DERIVATIVE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL BOND; CONFORMATION; CYCLIZATION; ELECTRON TRANSPORT; PHOTOCHEMISTRY; PROBABILITY; SYNTHESIS;

EID: 4043129759     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300585     Document Type: Article

References (44)

1. K.-D. Warzecha, X. Xing, M. Demuth, Pure Appl. Chem. 1997, 69, 109-112.
2. K.-D. Warzecha, X. Xing, M. Demuth, R. Goddard, M. Kessler, C. Krüger, Helv. Chim. Acta 1995, 78, 2065-2076.
3. Y. Orihara, J.-W. Yang, N. Komiya, K. Koge, T. Yoshikawa, Phytochemistry 2002, 59, 385-389.
4. I. Ara, B. S. Siddiqui, S. Faizi, S. Siddiqui, J. Nat. Prod. 1990, 53, 816-820.
5. Y. Takaishi, N. Wariishi, H. Tateishi, K. Kawazoe, K. Miyagi, K. Li, H. Duan, Phytochemistry 1997, 45, 979-984.
6. R. Fujita, H. Duan, Y. Takaishi, Phytochemistry 2000, 53, 715-722.
7. Antioxidant: H. Haragushi, H. Ishikawa, I. Kubo, Planta Med. 1997, 65, 213-215.
8. Cathartic and emetic: G. Appendino, E. Belloro, G. C. Tron, J. Jakupovic, M. Ballero, Fitoterapia 2000, 71, 134-142.
9. Anti-tumoral: Y. Takaishi, N. Wariishi, H. Tateishi, K. Kawazoe, K. Nakano, Y. Ono, H. Tokuda, H. Nishino, A. Iwashima, Phytochemistry 1997, 45, 969-974.
10. Abietatrien-3β-ol: J. G. Urones, I. S. Marcos, J. F. Ferreras, P. B. Barcala, Phytochemistry 1988, 27, 523-526. Micrandrol: M. A. De Alvarenga, J. J. Da Silva, H. E. Gottlieb, O. R. Gottlieb, Phytochemistry 1981, 20, 1159-1161. Totaradiol: H. Haraguchi, H. Ishikawa, I. Kubo, Planta Med. 1997, 213-215.
11. Abietatrien-3β-ol: J. G. Urones, I. S. Marcos, J. F. Ferreras, P. B. Barcala, Phytochemistry 1988, 27, 523-526. Micrandrol: M. A. De Alvarenga, J. J. Da Silva, H. E. Gottlieb, O. R. Gottlieb, Phytochemistry 1981, 20, 1159-1161. Totaradiol: H. Haraguchi, H. Ishikawa, I. Kubo, Planta Med. 1997, 213-215.
12. Abietatrien-3β-ol: J. G. Urones, I. S. Marcos, J. F. Ferreras, P. B. Barcala, Phytochemistry 1988, 27, 523-526. Micrandrol: M. A. De Alvarenga, J. J. Da Silva, H. E. Gottlieb, O. R. Gottlieb, Phytochemistry 1981, 20, 1159-1161. Totaradiol: H. Haraguchi, H. Ishikawa, I. Kubo, Planta Med. 1997, 213-215.
13. V. Rosales, J. L. Zambrano, M. Demuth, J. Org. Chem. 2002, 67, 1167-1170.
14. P. G. Gassman, K. J. Bottorf, J. Am. Chem. Soc. 1987, 109, 7547-7548.
15. K.-D. Warzecha, H. Görner, M. Demuth, J. Chem. Soc., Faraday Trans. 1998, 94, 1701-1706.
16. Previously reported X-ray data for 20: J. Y. Lallemand, M. Julia, D. Mansuy, Tetrahedron Lett. 1973, 45, 4461-4464.
17. Published separately in: J. L. Zambrano, V. Rosales, H. Schucht, T. Weyhermüller, M. Demuth, J. Chem. Crystallogr. 2002,52,391-394.
18. C. Heinemann, X. Xing, K.-D. Warzecha, P. Ritterskamp, H. Görner, M. Demuth, Pure Appl. Chem. 1998, 70, 2167-2176.
19. S. Handa, G. Pattenden, J. Chem. Soc., Perkin Trans, 1 1999, 843-845.
20. G. Stork, A. W. Burgstahler, J. Am. Chem. Soc. 1955, 5068-5077. A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni, Helv. Chim. Acta 1955, 38, 1890-1904.
21. G. Stork, A. W. Burgstahler, J. Am. Chem. Soc. 1955, 5068-5077. A. Eschenmoser, L. Ruzicka, O. Jeger, D. Arigoni, Helv. Chim. Acta 1955, 38, 1890-1904.
22. H. Weng, C. Scarlata, H. D. Roth, J. Am. Chem. Soc. 1996, 118, 10947-10953.
23. C. Heinemann, K.-D. Warzecha, X. Xing, M. Demuth, Indian J. Chem., Sect. A 1997, 36, 494-497.
24. P. G. Gassman, K. J. Bottorff, Tetrahedron Lett. 1987, 28, 5449-5452.
25. C. Heinemann, M. Demuth, J. Am. Chem. Soc. 1999, 121, 4894-4895.
26. [23a] S. L. Mattes, S. Farid, J. Am Chem. Soc. 1986, 108, 7356-736].
27. [23b] A. J. Moroulis, D. R. Arnold, Synthesis 1979, 819-820.
28. [23c] M. Demuth, H. Icil, M. Ozser, manuscript in preparation.
29. D. A. Connor, D. R. Arnold, P. K. Bakshi, T. S. Cameron, Can. J. Chem. 1995, 73, 762-771.
30. H. Zipse, J. Am. Chem. Soc. 1995, 117, 11798-11806.
31. B. B. Snider, Chem. Rev. 1996, 96, 339-363.
32. B. B. Snider, R. Nohan, S. A. Kates, J. Org. Chem. 1985, 50, 3659-3661.
33. P. D. Curran, Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon, New York, 1991, vol. 4.
34. D. Mansuy, M. Julia, Bull. Soc. Chim. Fr. 1972, 2689-2695.
35. J. X. Xing, M. Demuth, Synlett 1999, 987-990.
36. J. Den Heijer, O. B. Shadid, J. Cornelisse, E. Havinga, Tetrahedron 1977, 33, 779-786.
37. I. Abe, M. Rohmer, G. D. Prestwich, Chem. Rev. 1993, 93, 2189-2206.
38. H. Beierbeck, J. K. Saunders, J. W. ApSimon, Can. J. Chem. 1977, 55, 2813-2828. P. E. Hammann, H. Kluge, G. G. Habermehl, Magn. Reson. Chem. 1991, 29, 133-136.
39. H. Beierbeck, J. K. Saunders, J. W. ApSimon, Can. J. Chem. 1977, 55, 2813-2828. P. E. Hammann, H. Kluge, G. G. Habermehl, Magn. Reson. Chem. 1991, 29, 133-136.
40. J. M. Miguel Del Corral, M. Gordaliza, M. A. Salinero, A. San Feliciano, Magn. Reson. Chem. 1994, 32, 774-781.
41. J. A. Elings, R. S. Downing, R. A. Sheldon, Eur. J. Org. Chem. 1999, 837-846.
42. S. Ghosh, A. K. Ghosh, U. R. Ghatak, Synth. Commun. 1992, 22, 553-564.
43. H. Suzuki, T. Hanafusa, Synthesis 1974, 53-55. H. Suzuki, K. Nakamura, R. Goto, Bull. Chem. Soc. Jpn. 1966, 39, 128-131.
44. H. Suzuki, T. Hanafusa, Synthesis 1974, 53-55. H. Suzuki, K. Nakamura, R. Goto, Bull. Chem. Soc. Jpn. 1966, 39, 128-131.