Formal total synthesis of (±)-dimethyl secologanoside

Journal of the Chinese Chemical Society

Volumn 50, Issue 3 A, 2003, Pages 441-444

  Tai, Huo Mu ^a   Huang, Ming Hsing ^a   Yang, Chau Chen ^a  

^a CHIA NAN UNIVERSITY OF PHARMACY AND SCIENCE   (Taiwan)

Author keywords

Cyclopentanopyran; Iridoid monoterpene; Norrish I type fragmentation; Secologanoside

Indexed keywords

EID: 34247220076     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200300069     Document Type: Article

References (38)

1. For reviews see: (a) Grayson, D. H. Nat. Prod. Rep. 1996, 13, 195.
2. (b) Grayson, D. H. Nat. Prod. Rep. 1994, 77, 225.
3. (c) Boros, C. A.; Stermitz, F. R. J. Nat. Prod. 1991, 54, 1173.
4. (d) Boros, C. A.; Stermitz, F. R. J. Nat. Prod. 1990, 53, 1055.
5. (e) EI-Naggar, L. J.; Bwal, J. L. J. Nat. Prod, 1980, 43, 649.
6. (a) Hewson, A. T.; MacPherson, D. T. J. Chem. Soc. Perkin Trans. I 1985, 2625.
7. (b) Hewson. A. T.; MacPherson, D. T. Tetrahehron Lett. 1983, 5807.
8. (c) Chang, C.-P.; Yin, W.-K.; Chang, N.-C. J. Chin. Chem. Soc. 1994, 41, 613.
9. (d) Tai, H.-M.; Chang, M.-Y.; Lee, A.-Y.; Chang, N.-C. J. Org. Chem. 1999, 64, 659.
10. (e) Tai, H.-M.; Yang, C.-C. J. Chin. Chem. Soc. 2000, 47, 929.
11. (f) Tai, H.-M.; Yang, C.-C.; Yeh, M.-L.; Chang, N.-C. J. Chin. Chem. Soc. 2001, 48, 901.
12. (a) For reviews about secologanin: Tietze, L.-F. Angew. Chem., Int. Ed. Engl. 1983, 828.
13. (b) Tietze L.-F.; Meier, H.; Nutt, H. Liebigs Ann. Chem. 1990, 253.
14. (c) Calis, I.; Sticher, D. Phytochemistry 1984, 23, 2539.
15. (d) Inoue, K.; Inouye, H.; Takaishi, T.; Kuwajima, H. Phytochemistry 1989, 28, 2971.
16. (e) Aimi, N.; Seki, H.; Sakai, S.-J. Chem. Pharm. Bull. 1992, 40, 2588.
17. (f) Yamamoto, H.; Katano, N.; Ooi, A,; Inoue, K. Phytochemistry 1999, 50, 417.
18. (a) Inoue, K.; Ono, N.; Nakajima, H.; Fujie, I.; Inouye, H.; Fujita, T. Herocycles 1992, 53, 1055.
19. (b) Damtoft, S.; Franzyk, H.; Jensen, S. Phytochemistry 1993, 34, 1291.
20. (c) Kutchan, T. M. Phytochemistry 1993, 32, 493.
21. (d) Trost, B. M.; Mao, M. K.-T.; Balkovec, J. M.; Buhlmayer, P. J. Am. Chem. Soc. 1986, 108, 4965.
22. (a) Tietze, L. F.; Baertels, C. Tetrahedron 1989, 45, 681.
23. (b) Tan, R. X.; Wolfender, J.-L.; Zhang, L. X.; Ma, W. G.; Fuzzati, N. Phytochemistry 1996, 42, 1305.
24. (a) Tan, R. X.; Wolfender, J.-L.; Zhang, L. X.; Ma, W. G.; Fuzzati, N. Phytochemistry 1996, 42, 1305.
25. (b) Tan, R. X.; Wolfender, J.-R.; Ma, W. G.; Zhang, L. X.; Hostettmann, K. Phytochemistry 1996, 41, 111.
26. For reviews see: (a) Nangia, A.; Prasuna, G.; Rao, P. B. Tetrahedron 1997, 53, 14507.
27. (b) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Heideberg, 1987, 112.
28. (c) ApSimon, J. The Total Synthesis of Natural. Products; Wiley: New York, 1988, Vol 7; 339.
29. (d) ApSimon, J. The Total Synthesis of Natural Products; Wiley: New York, 1981, Vol 4; 494.
30. (e) ApSimon, J. The Total Synthesis of Natural Products; Wiley: New York, 1973, Vol 2; 62.
31. Chang, N.-C.; Day, H.-M.; Lu, W.-F. J. Org. Chem. 1989, 54, 4083.
32. (a) Arai, Y.; Kawanami, S.; Koizumi, T. Chem. Lett. 1990, 1585.
33. (b) Meinwald, J.; Chapman, R. A. J. Am. Chem. Soc.1968, 90, 3218.
34. (c) Furuichi, K.; Abe, K.; Miwa, T. Terahedron Lett. 1974, 3685.
35. Wilder, Jr. P.; Portis, Jr. A. R.; Wright, G. W.; Shepherd, J. M. J. Org. Chem. 1914, 39, 1636.
36. (a) Henne, A. L.; Hill, P. J. Am. Chem. Soc. 1943, 65, 752.
37. (b) Lee, A.-Y.; Chang, M.-Y.; Chang, N.-C. Heterocycles 1999, 51, 295.
38. (c) Lee, A.-Y.; Chang, M.-Y.; Tai, H.-M.; Chang, N.-C. J. Chin. Chem. Soc. 1999, 46, 937-937.