Practical and efficient entry to isoflavones by Pd(0)/C-mediated Suzuki-Miyaura reaction. Total synthesis of geranylated isoflavones

Tetrahedron

Volumn 63, Issue 14, 2007, Pages 3010-3016

  Felpin, François Xavier ^a   Lory, Cécile ^a   Sow, Hawaa ^a   Acherar, Samir ^a  

^a UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

7 O Geranylformononetin; Conrauinone D; Griffonianone D; Isoflavones; Pd C; Suzuki Miyaura reaction

Indexed keywords

7 O GERANYLFORMONONETIN; CARBON; CONRAUINONE D; GRIFFONIANONE D; ISOFLAVONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; DIHYDROXYLATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; MITSUNOBU REACTION; PRIORITY JOURNAL; QUANTUM YIELD; REACTION ANALYSIS; SUZUKI MIYAURA REACTION;

EID: 33847260626     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.062     Document Type: Article

References (44)

1. Couladis M., Baziou P., Verykokidou E., and Loukis A. Phytother. Res. 16 (2002) 769-770
2. Booth C., Hargreaves D.F., Hadfield J.A., McGown A.T., and Potten C.S. Br. J. Cancer 80 (1999) 1550-1557
3. Vasselin D.A., Westwell A.D., Matthews C.S., Bradshaw T.D., and Stevens M.F.G. J. Med. Chem. 49 (2006) 3973-3981
4. Chacko B.K., Chandler R.T., Mundhekar A., Khoo N., Pruitt H.M., Kucik D.F., Parks D.A., Kevil C.G., Barnes S., and Patel R.P. Am. J. Physiol. Heart Circ. Physiol. 289 (2005) H908-H915
5. Bennetau-Pelissero C., Le Houérou C., Lamothe V., Le Menn F., Babin P., and Bennetau B. J. Agric. Food Chem. 48 (2000) 305-311
6. Le Houérou C., Bennetau-Pelissero C., Lamothe V., Le Menn F., Babin P., and Bennetau B. Tetrahedron 56 (2000) 295-301
7. Doerge D.R., and Sheehan D.M. Environ. Health Perspect. 110 (2002) 349-353
8. Duncan A.M., Phipps W.R., and Kurzer M.S. Best Pract. Res. Clin. Endocrinol. Metab. 17 (2003) 253-271
9. Boland G.M., and Donnelly D.M.X. Nat. Prod. Rep. 15 (1998) 241-260
10. Felpin F.-X. J. Org. Chem. 70 (2005) 8575-8578
11. For a review, see:. Felpin F.-X., Ayad T., and Mitra S. Eur. J. Org. Chem. (2006) 2679-2690
12. Hosny M., and Rosazza J.P.N. J. Nat. Prod. 62 (1999) 853-858
13. Chang Y., Nair M., Santell R., and Helferich W. J. Agric. Food Chem. 42 (1994) 1869-1871
14. Gammil R.B. Synthesis (1979) 901-903
15. For the synthesis of isoflavones by Suzuki-Miyaura cross-coupling, see:
16. Hoshino Y., Miyaura N., and Suzuki A. Bull. Chem. Soc. Jpn. 61 (1988) 3008-3010
17. Yokoe I., Sugita Y., and Shirataki Y. Chem. Pharm. Bull. 37 (1989) 529-530
18. Joo Y.H., Kim J.K., Kang S.-H., Noh M.-S., Ha J.-Y., Choi J.K., Lim K.M., Lee C.H., and Chung S. Bioorg. Med. Chem. Lett. 13 (2003) 413-417
19. Ding K., and Wang S. Tetrahedron Lett. 46 (2005) 3707-3709
20. Ito F., Iwasaki M., Watanabe T., Ishikawa T., and Higuchi Y. Org. Biomol. Chem. 3 (2005) 674-681
21. Eisnor C.R., Gossage R.A., and Yadav P.N. Tetrahedron 62 (2006) 3395-3401
22. For leading examples of Suzuki-Miyaura reactions with Pd/C as catalyst, see:
23. Marck G., Villiger A., and Buchecker R. Tetrahedron Lett. 35 (1994) 3277-3280
24. Gala D., Stamford A., Jenkins J., and Kugelman M. Org. Process Res. Dev. 1 (1997) 163-164
25. Ennis D.S., McManus J., Wood-Kaczmar W., Richardson J., Smith G.E., and Carstairs A. Org. Process Res. Dev. 3 (1999) 248-252
26. LeBlond C.R., Andrews A.T., Sun Y., and Sowa Jr. J.R. Org. Lett. 3 (2001) 1555-1557
27. Dyer U.C., Shapland P.D., and Tiffin P.D. Tetrahedron Lett. 42 (2001) 1765-1767
28. McClure M.S., Roschangar F., Hodson S.J., Millar A., and Osterhout M.H. Synthesis (2001) 1681-1685
29. Organ M.G., and Mayer S. J. Comb. Chem. 5 (2003) 118-124
30. Tagata T., and Nishida M. J. Org. Chem. 68 (2003) 9412-9415
31. Gruber M., Chouzier S., Koheler K., and Djakovitch L. Appl. Catal., A: Gen. 265 (2004) 161-169
32. Lu G., Franzén R., Zhang Q., and Xu Y. Tetrahedron Lett. 46 (2005) 4255-4259
33. Arvela R.K., and Leadbeater N.E. Org. Lett. 7 (2005) 2101-2104
34. Lysén M., and Köhler K. Synlett (2005) 1671-1674
35. Dagne E., Bekele A., Noguchi H., Shibuya M., and Sankawa U. Phytochemistry 29 (1990) 2671-2673
36. Yankep E., Fomum Z.T., and Dagne E. Phytochemistry 46 (1997) 591-593
37. Fuendjiep V., Nkengfack A.E., Fomum Z.T., Sondengam B.L., and Bodo B. Phytochemistry 47 (1998) 113-115
38. Yankep E., Fomum Z.T., Bisrat D., Dagne E., Hellwig V., and Steglich W. Phytochemistry 49 (1998) 2521-2523
39. Yankep E., Njamen D., Fotsing M.T., Fomum Z.T., Mbanya J.-C., Giner R.M., Recio M.C., Máñez S., and Ríos J.L. J. Nat. Prod. 66 (2003) 1288-1290
40. Vidari G., Di Rosa A., Castronovo F., and Zanoni G. Tetrahedron: Asymmetry 11 (2000) 981-989
41. Enantiomeric excess could not be determined at this stage and was measured by chiral HPLC on griffonianone D 2 itself, see Section 4 for details.
42. Mitsunobu O. Synthesis (1981) 1-28
43. Fukai T., Wang Q.-H., Inami R., and Nomura T. Heterocycles 31 (1990) 643-650
44. Watson I.D.G., Styler S.A., and Yudin A.K. J. Am. Chem. Soc. 126 (2004) 5086-5087