Progress in the Total Synthesis of Styryllactone Natural Products

Chinese Journal of Organic Chemistry

Volumn 23, Issue 11, 2003, Pages 1177-1184

  Zhang, Xing Xian ^a   Li, Wei Dong ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

Natural product; Styryllactone; Total synthesis

Indexed keywords

LACTONE DERIVATIVE; METHANOL DERIVATIVE; NATURAL PRODUCT; STYRYLLACTONE; UNCLASSIFIED DRUG;

CHEMICAL REACTION; LACTONIZATION; OXIDATION; REVIEW; RING CLOSING METATHESIS;

EID: 0347655441     PISSN: 02532786     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (51)

1. Wu, Y. C.; Duh, C. Y.; Chang, F. R.; Chang, G. Y.; Wang, S. K.; Chang, J. J.; Mephail, D. R.; Mcphail, A. T.; Lee, K. H. J. Nat. Prod. 1991, 54, 1077.
2. Talapatra, S. K.; Basu, D.; Deb, F.; Goswami, S.; Talapatra, B. Indian J. Chem. 1985, 24B, 29.
3. Sam, T. W.; Yeu, C. S.; Matsjeh, S.; Gan, E. K.; Razak, D.; Mohamed, A. I. Tetrahedron Lett. 1987, 28, 2544.
4. Geran, R. I.; Greenberg, N. H.; MacDonald, M. M.; Schumacher, A. M.; Abbott, B. J. Cancer Chemother. Res. 1972, 3, 1.
5. (a) Blazquez, M. A.; Bermejo, A.; Zasfra, M. C.; Cortes, D. Phytochem. Anal. 1999, 10, 161.
6. (b) Bermejo, A.; Blazquez, M. A.; Rao, K. S.; Cortes, D. Phytochem. Anal. 1999, 10, 127.
7. (c) Yasui, K.; Tamura, Y.; Nakatani, T.; Kawada, K.; Ohtani, M. J. Org. Chem. 1995, 60, 7567.
8. (d) Fang, X.-P.; Anderson, J. E.; Chang, C.-J.; MaLaughlin, J. L.; Fanwick, P. E. J. Nat. Prod. 1991, 54, 1034.
9. (e) Argoudelis, A. D.; Zieserl, J. F. Tetrahedron Lett. 1966, 18, 1969.
10. (f) For a review of 5,6-dihydro-2H-pyran-2-ones, see: Davies-Coleman, M. T.; Riviett, D. E. A. In Progress in the Chemistry of Organic Natural Products , Eds.: Herz, W.; Grisebach, H.; Kirby, G. W.; Tamm, C., Springer, New York, 1989, Vol. 55, pp. 1-35.
11. Georgiadis, M. P.; Couladouros, E. A.; Polissiou, M. G. J. Org. Chem. 1982, 47, 3054 and references cited therein.
12. Kusakabe, M.; Kitano, Y.; Kobayashi, Y.; Sato, F. J. Org. Chem. 1988, 53, 1586.
13. Honda, T.; Kametani, T.; Kanai, K.; Tatsuzaki, Y.; Tsubuki, M. J. Chem. Soc., Perkin Trans. 1 1990, 1733.
14. Yang, Z. C.; Jiang, X. B.; Wang, Z. M.; Zhou, W. S. J. Chem. Soc. , Perkin Trans. 1 1997, 317.
15. Peng, X. S.; Li, A. P.; Lu, J. P.; Pan. X. F. Tetrahedron 2002, 58, 6799.
16. (a) Harris, J. M.; O'Doherty, G. A. Org. Lett. 2000, 2, 2983.
17. (b) Harris, J. M.; O'Doherty, G. A. Tetrahedron 2001, 57, 5161.
18. Tsubuki, M.; Kanai, K.; Nagase, H.; Honda, T. Tetrahedron 1999, 55, 2493 and references cited therein.
19. (a) Amstrong, S. K. J. Chem. Soc. , Perkin Trans. 1 1998, 371.
20. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
21. (c) Furstner, A. Angew. Chem. , Int. Ed. 2000, 39, 3013.
22. Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron Lett. 1998, 39, 4651.
23. Srikanth, G. S. C.; Krishna, U. M.; Trivedi, G. K. Tetrahedron Lett. 2002, 43, 5471.
24. Ramachandran, P. V.; Reddy, M. V. R.; Brown, H. C. Tetrahedron Lett. 2000, 41, 583.
25. Ghosh, A. K.; Bilcer, G. Tetrahedron Lett. 2000, 41, 1003.
26. Trost, B. M.; Yeh, V. S. C. Org. Lett. 2002, 4, 3513.
27. (a) Gesson, J. P.; Jacquesy, J. C.; Mondon, M. Tetrahedron Lett. 1987, 28, 3945.
28. (b) Gesson, J. P.; Jacquesy, J. C.; Mondon, M. Tetrahedron 1989, 45, 2627.
29. Kang, S. H.; Kim, W. J. Tetrahedron Lett. 1989, 30, 5915.
30. Chen, J.; Lin, G. Q.; Wang, Z. M.; Lin, H. A. Synlett 2002, 8, 1265.
31. Job, A.; Wolberg, M.; Müller, M.; Ender, D. Synlett 2001, 11, 1796.
32. Shing, T. K. M.; Gillhouley, J. G. Tetrahedron 1994, 50, 8685.
33. Shing, T. K. M.; Tsui, H. C.; Zhou, Z. H. J. Org. Chem. 1995, 60, 3121.
34. Yi, X. H.; Meng, Y.; Hua, X. G.; Li, C. J. J. Org. Chem. 1998, 63, 7472.
35. (a) Mukai, C.; Hirai, S.; Kim, I. J.; Hanaoka, M. Tetrahedron Lett. 1996, 37, 5389.
36. (b) Mukai, C.; Hirai, S.; Hanaoka, M. J. Org. Chem. 1997, 62, 6619.
37. Somfai, P. Tetrahedron 1994, 50, 11315.
38. Gracza, T.; Jäger, V. Synlett 1992, 3, 191.
39. Zhang, X. X. Ph. D. Dessertation, Lanzhou University, Lanzhou, 2002 (in Chinese).
40. Li, W.-D. Z.; Zhang, X.-X. Org. Lett. 2002, 4, 3485.
41. (a) Roth, B. D.; Roark, W. H. Tetrahedron Lett. 1988, 29, 1255.
42. (b) Ichikawa, Y.; Isobe, M.; Bai, D.-L.; Goto, T. Tetrahedron 1987, 43, 4737.
43. (c) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
44. Honda, T.; Horichi, S.; Mizutoni, H.; Kanai, K. J. Org. Chem. 1996, 61, 4944.
45. (a) Lichtenthaler, F. W.; Lorenz, K. Tetrahedron Lett. 1987, 28, 47.
46. (b) Lorenz, K.; Lichtenthaler, F. W. Tetrahedron Lett. 1987, 28, 6437.
47. (c) Valverde, S.; Hernandez, A.; Herradon, B.; Rabanal, R. M.; Martin-Lomas, M. Tetrahedron 1987, 43, 3499.
48. Takano, D.; Nagamitsu, T.; Ui, H.; Shiomi, K.; Yamaguchi, Y.; Masuma, R. ; Kuwajima, I.; Omura, S. Org. Lett. 2001, 3, 2289.
49. Jiang, B.; Chen, Z. L. Tetrahedron: Asymmetry 2001, 12, 2835.
50. (a) Kalesse, M.; Quitschalle, M.; Khandavalli, C. P.; Saeed, A. Org. Lett. 2001, 3, 3107.
51. (b) Quitschalle, M.; Christmann, M.; Bhatt, U,; Kalesse, M. Tetrahedron Lett. 2001, 42 , 1263.