An efficient asymmetric synthesis of furofuran lignans: (+)-Sesamin and (-)-sesamin

Tetrahedron Asymmetry

Volumn 17, Issue 1, 2006, Pages 3-6

  Kim, Ju Cheun ^a   Kim, Kwang Hyun ^a   Jung, Jae Chul ^b   Park, Oee Sook ^a  

^a Chungbuk National University   (South Korea)

^b UNIVERSITY OF MISSISSIPPI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; EUDESMIN; LIGNAN DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PIPERONAL; SESAMIN; UNCLASSIFIED DRUG; YANGAMBIN;

ALDOL REACTION; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 30944433783     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.11.007     Document Type: Article

References (44)

1. R.S. Ward Chem. Soc. Rev. 11 1982 75 125
2. R.S. Ward Nat. Prod. Rep. 10 1993 1 28
3. R.S. Ward Nat. Prod. Rep 12 1995 183 205
4. R.S. Ward Nat. Prod. Rep. 14 1997 143 174
5. R.S. Ward Nat. Prod. Rep 16 1999 75 96
6. D.A. Whiting Nat. Prod. Rep. 7 1990 349 364
7. E. Okuyama, K. Suzumura, and M. Yamazaki Chem. Pharm. Bull. 43 1995 2200 2204
8. K. Hashimoto, T. Yanagisawa, Y. Okui, Y. Ikeya, M. Maruno, and T. Fujita Planta Med. 60 1994 124 127
9. M. Takasaki, T. Konoshima, I. Yasuda, T. Hamano, and H. Tokuda Biol. Pharm. Bull. 20 1997 776 780
10. Y.M. Chiung, H. Hayashi, H. Matsumoto, T. Otani, K. Yoshida, M.Y. Huang, R.X. Chen, J.R. Liu, and M. Nakayama J. Antibiot. 47 1994 487 491
11. W.D. MacRae, and G.H.N. Towers Phytochemistry 23 1984 1207 1220
12. R.C. Brown, C.J. Bataille, G. Bruton, J.D. Hinks, and N.A. Swain J. Org. Chem. 66 2001 6719 6728
13. S. Iwakami, Y. Ebizuka, and U. Sankawa Heterocycles 30 1990 795 798
14. S. Iwakami, J.B. Wu, Y. Ebizuka, and U. Sankawa Chem. Pharm. Bull. 40 1992 1196 1198
15. K. Ichikawa, T. Kinoshita, S. Nishibe, and U. Sankawa Chem. Pharm. Bull. 34 1986 3514 3517
16. Isolation: S.H. Bertram Biochem. Zeit. 197 1928 433 441
17. Structure: W.D. Cohen Rec. Trav. Chem. 57 1938 653 658
18. F. Von Bruchhausen, and H. Gerhard Ber. 72B 1939 830 838
19. Stereochemistry: E.D. Becker, and M. Beroza Tetrahedron Lett. 1962 157 163
20. M. Beroza, and M.S. Schechter J. Am. Chem. Soc. 78 1956 1242 1247
21. A. Pelter, R.S. Ward, D.J. Watson, P. Collins, and I.T. Kay J. Chem. Soc., Perkin Trans. 1 1982 175 181
22. E.C. Taylor, J.G. Andrade, G.J.H. Rall, K. Steliou, G.E. Jagdmann Jr., and A. McKillop J. Org. Chem. 46 1981 3078 3081
23. S. Takano, T. Ohkawa, S. Tamori, S. Satoh, and K. Ogasawara J. Chem. Soc., Chem. Commun. 1988 189 191
24. K. Orito, K. Yorita, and H. Suginome Tetrahedron Lett. 32 1991 5999 6002
25. H. Suginome, M. Ishikawa, K. Yorita, N. Shimoyama, T. Sasaki, and K. Orito J. Org. Chem. 60 1995 3052 3064
26. T. Takeya, Y. Ara, and S. Tobinaga Chem. Pharm. Bull. 43 1995 1970 1976
27. K. Samizu, and K. Ogasawara Chem. Lett. 1995 543 544
28. H.M. Hull, R.G. Jones, and D.W. Knight J. Chem. Soc., Perkin Trans. 1 1998 1779 1788
29. A. Pelter, R.S. Ward, D.J. Watson, and I.R. Jack J. Chem. Soc., Perkin Trans. 1 1982 183 190
30. N.A. Swain, R.C.D. Brown, and G. Bruton J. Org. Chem. 69 2004 122 129
31. D.J. Aldous, A.J. Dalencon, and P.G. Steel J. Org. Chem. 68 2003 9159 9161
32. S.C. Roy, K.K. Rana, and C. Guin J. Org. Chem. 67 2002 3242 3248
33. J.B. Davenport, and M.D. Sutherland Aust. J. Chem. 7 1954 384 386
34. H. Ina, A. Asai, H. Iida, and T. Ushida Planta Med. 53 1987 228
35. +, found: 383.0695.
36. J.R. Gage, and D.A. Evans Org. Synth. 68 1990 77 82
37. D.A. Evans, J. Bartroli, and T.L. Shih J. Am. Chem. Soc. 103 1981 2127 2129
38. D.A. Evans, D.L. Rieger, M.T. Bilodeau, and F. Urpi J. Am. Chem. Soc. 113 1991 1047 1049
39. D.E. Van Horn, and S. Masamune Tetrahedron Lett. 24 1979 2229 2232
40. T.H. Yan, C.W. Tan, H.C. Lee, H.C. Lo, and T.Y. Huang J. Am. Chem. Soc. 115 1993 2613 2621
41. F. Kido, K. Tsutsumi, R. Maruta, and A. Yoshikoshi J. Am. Chem. Soc. 101 1979 6420 6424
42. F. Kido, R. Maruta, K. Tsutsumi, and A. Yoshikoshi Chem. Lett. 1979 311 312
43. J.L. Fry, M. Orfanopoulos, M.G. Adlington, W.P. Dittman Jr., and S.B. Silverman J. Org. Chem. 43 1978 374 375;
44. S. Quideau, and J. Ralph J. Chem. Soc., Perkin Trans. 1 1993 653 659