Stereoselective total synthesis of furofuran lignans through dianion aldol condensation

Tetrahedron Letters

Volumn 47, Issue 36, 2006, Pages 6433-6437

  Jung, Jae Chul ^a   Kim, Ju Cheun ^a   Moon, Hyung In ^b   Park, Oee Sook ^c  

^a UNIVERSITY OF MISSISSIPPI   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c Chungbuk National University   (South Korea)

Author keywords

(+) Eudesmin; (+) Yangambin; ( ) Eudesmin; ( ) Yangambin; Furofuran lignans; Intramolecular ring cyclization; Stereoselective aldol condensation

Indexed keywords

EUDESMIN; FURAN DERIVATIVE; LIGNAN; UNCLASSIFIED DRUG; YANGAMBIN;

ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 33746652877     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.127     Document Type: Article

References (49)

1. Ward R.S. Chem. Soc. Rev. 11 (1982) 75-125
2. Ward R.S. Nat. Prod. Rep. 10 (1993) 1-28
3. Ward R.S. Nat. Prod. Rep. 12 (1995) 183-205
4. Ward R.S. Nat. Prod. Rep. 14 (1997) 143-174
5. Ward R.S. Nat. Prod. Rep. 16 (1999) 75-96
6. Whiting D.A. Nat. Prod. Rep. 7 (1990) 349-364
7. Teles H.L., Hemerly J.P., Paulettit P.M., Pandolfi J.R.C., Araujot A.R., Valentini S.R., Young M.C.M., Bolzani V.S., and Silva D.H.S. Nat. Prod. Res. 19 (2005) 319-323
8. Chiung Y.M., Hayashi H., Matsumoto H., Otani T., Yoshida K., Huang M.Y., Chen R.X., Liu J.R., and Nakayama M. J. Antibiot. 47 (1994) 487-491
9. De Leon E.J., Olmedo D.A., Solis P.N., Gupta M.P., and Terencio M.C. Planta Med. 68 (2002) 1128-1131
10. Serra M.F., Diaz B.L., Barreto E.O., Pereira A.P.B., Lima M.C.R., Barbosa-Filho J.M., Cordeiro R.S.B., Martins M.A., and De Silva P.M.R. Planta Med. 63 (1997) 207-212
11. Hoang V.D., Tan G.T., Zhang H.J., Tamez P.A., Nguyen V.H., Nguyen M.C., Soejarto D.D., Fong H.H.S., and Pezzuto J.M. Phytochemistry 59 (2002) 325-329
12. Asano J., Chiba K., Tada M., and Yoshi T. Phytochemistry 42 (1996) 713-717
13. MacRae W.D., and Towers G.H.N. Phytochemistry 23 (1984) 1207-1220
14. Vermes B., Seligmann O., and Wagner H. Phytochemistry 30 (1991) 3087-3089
15. Brown R.C., Bataille C.J., Bruton G., Hinks J.D., and Swain N.A. J. Org. Chem. 66 (2001) 6719-6728
16. Iwakami S., Ebizuka Y., and Sankawa U. Heterocycles 30 (1990) 795-798
17. Iwakami S., Wu J.B., Ebizuka Y., and Sankawa U. Chem. Pharm. Bull. 40 (1992) 1196-1198
18. Ichikawa K., Kinoshita T., Nishibe S., and Sankawa U. Chem. Pharm. Bull. 34 (1986) 3514-3517
19. Nikaido T., Ohmoto T., Kinoshita T., Sankawa U., Nishibe S., and Hisada S. Chem. Pharm. Bull. 29 (1981) 3586-3592
20. Plante G.E., Prevost C., Chainey A., Braquet P., and Sirois P. Am. J. Physiol. 253 (1987) R375-R378
21. Bernard C.B., Arnason J.T., Philogene B.J.R., Lam J., and Waddell T. Phytochemistry 28 (1989) 1373-1377
22. Brown R.C.D., Bataille C.J.R., and Hinks J.D. Tetrahedron Lett. 42 (2001) 473-475
23. Van Oeveren A., Jansen J.F.G.A., and Feringa B.L. J. Org. Chem. 59 (1994) 5999-6007
24. Ogiku T., Yoshida S.I., Ohmizu H., and Iwasaki T. J. Org. Chem. 60 (1995) 1148-1153
25. Yoda H., Kimura K., and Takabe K. Synlett (2001) 400-402
26. Aldous D.J., Dalencon A.J., and Steel P.G. Org. Lett. 4 (2002) 1159-1162
27. Roy S.C., Rana K.K., and Guin C. J. Org. Chem. 67 (2002) 3242-3248
28. Swain N.A., Brown R.C.D., and Bruton G. J. Org. Chem. 69 (2004) 122-129
29. Pelter A., Ward R.S., Watson D.J., Collins P., and Kay I.T. J. Chem. Soc., Perkin Trans. 1 (1982) 175-181
30. Taylor E.C., Andrade J.G., Rall G.J.H., Steliou K., Jagdmann Jr. G.E., and McKillop A. J. Org. Chem. 46 (1981) 3078-3081
31. Takano S., Ohkawa T., Tamori S., Satoh S., and Ogasawara K. J. Chem. Soc., Chem. Commun. (1988) 189-191
32. Orito K., Yorita K., and Suginome H. Tetrahedron Lett. 32 (1991) 5999-6002
33. Suginome H., Ishikawa M., Yorita K., Shimoyama N., Sasaki T., and Orito K. J. Org. Chem. 60 (1995) 3052-3064
34. Takeya T., Ara Y., and Tobinaga S. Chem. Pharm. Bull. 43 (1995) 1970-1976
35. Samizu K., and Ogasawara K. Chem. Lett. (1995) 543-544
36. Hull H.M., Jones R.G., and Knight D.W. J. Chem. Soc., Perkin Trans. 1 (1998) 1779-1788
37. Pelter A., Ward R.S., Watson D.J., and Jack I.R. J. Chem. Soc., Perkin Trans. 1 (1982) 183-190
38. Beroza M., and Schechter M.S. J. Am. Chem. Soc. 78 (1956) 1242-1247
39. Kise N., Fujimoto A., and Ueda N. Tetrahedron: Asymmetry 13 (2002) 1845-1847
40. Aldous D.J., Dalencon A.J., and Steel P.G. J. Org. Chem. 68 (2003) 9159-9161
41. Kasahara H., Miyazawa M., and Kameoka H. Phytochemistry 44 (1997) 1479-1482
42. Banerjee B., and Roy S.C. Synthesis (2005) 2913-2919
43. Kim J.C., Kim K.H., Jung J.C., and Park O.S. Tetrahedron: Asymmetry 17 (2006) 3-6
44. Gage J.R., and Evans D.A. Org. Synth. 68 (1990) 77-82
45. Jung J.C., Kache R., Vines K.K., Zheng Y., Bijoy P., Valluri M., and Avery M.A. J. Org. Chem. 69 (2004) 9269-9284
46. Inoue T., Liu J.F., Buske D.C., and Abiko A. J. Org. Chem. 67 (2002) 5250-5256
47. Evans D.A., Clark J.S., Metternich R., Novack V.J., and Sheppard G.S. J. Am. Chem. Soc 112 (1990) 866-868
48. +, found: 475.1610.
49. Anjaneyulu A.S.R., Rao A.M., Rao V.K., Row L.R., Pelter A., and Ward R.S. Tetrahedron 33 (1977) 133-143