Synthesis of polyprenylated benzoylphloroglucinols by regioselective prenylation of phloroglucinol in an aqueous medium

European Journal of Organic Chemistry

Volumn , Issue 8, 2008, Pages 1358-1369

  Raikar, Sanjay B ^a   Nuhant, Philippe ^a   Delpech, Bernard ^a   Marazano, Christian ^a  

^a CNRS   (France)

Author keywords

Biomimetic synthesis; C benzoylation; Electrophilic cyclization; Natural products; Phloroglucinols; Prenylation

Indexed keywords

EID: 53749105476     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701009     Document Type: Article

References (48)

1. For a review, see: I. P. Singh, S. B. Bharate, Nat. Prod. Rep. 2006, 23, 558-591.
2. For a review, see: R. Ciochina, R. B. Grossman, Chem. Rev. 2006, 106, 3963-3986.
3. O. Cuesta-Rubio, H. Velez-Castro, B. A. Frontana-Uribe, J. Cardenas, Phytochemistry 2001, 57, 279-283.
4. D. Roux, H. A. Hadi, S. Thoret, D. Guénard, O. Thoison, M. Païs, T. Sévenet, J. Nat. Prod. 2000, 63, 1070-1076.
5. W. Hamed, S. Brajeul, F. Mahuteau-Betzer, O. Thoison, S. Mons, B. Delpech, N. V. Hung, T. Sévenet, C. Marazano, J. Nat. Prod. 2006, 69, 774-777.
6. a) P. Nuhant, M. David, T. Pouplin, B. Delpech, C. Marazano, Org. Lett. 2007, 9, 287-289;
7. for a similar approach, see: b) V. Rodeschini, N. M. Ahmad, N. S. Simpkins, Org. Lett. 2006, 8, 5283-5285;
8. for other recent clusianone syntheses, see: c) J. Qi, J. A. Porco Jr, J. Am. Chem. Soc. 2007, 129, 12682-12683;
9. d) C. Tsukano, D. R. Siegel, S. J., Danishefsky, Angew. Chem. Int. Ed., DOI: 10.1002/anie.200703886.
10. T. Pouplin, B. Tolon, P. Nuhant, B. Delpech, C. Marazano, Eur. J. Org. Chem. 2007, 5117-5125.
11. S. Brajeul, B. Delpech, C. Marazano, Tetrahedron Lett. 2007, 48, 5597-5600.
12. K. C. Nicolaou, G. Vassilikogiannakis, T. Montagnon, Angew. Chem. Int. Ed. 2002, 41, 3276-3281.
13. For mono- and meta-diprenylation in the presence of potassium hydroxide in water, see, for example: a) T. Meikle, R. Stevens, J. Chem. Soc. Perkin Trans. 1 1978, 1303-1312;
14. b) L. Xiao, W. Tan, Y. Li, Synth. Commun. 1998, 28, 2861-2869;
15. for triprenylation in the presence of sodium methoxide in methanol, see: c) W. Riedl, Chem. Ber. 1952, 85, 692-710;
16. for triprenylation in liquid ammonia, see: d) K. G. Drewett, D. R. J. Laws, J. Inst. Brew. 1970, 76, 188-190;
17. e) M. Collins, D. R. J. Laws, J. D. McGuinness, J. A. Elvidge, J. Chem. Soc. C 1971, 3814-3818;
18. for polyprenylation in the presence of a strongly basic ion-exchange resin in benzene, see: f) M. Collins, D. R. J. Laws, J. Chem. Soc. Perkin Trans. 1 1973, 2013-2015.
19. R. J. Molyneux, L. Jurd, Tetrahedron 1970, 26, 4743-4751.
20. H.-H. Lee, J. Chem. Soc. Perkin Trans. 1 1981, 3205-3213.
21. E. Collins, G. D. John, P. V. R. Shannon, J. Chem. Soc. Perkin Trans. 1 1975, 96-101.
22. A. Gissot, A. Wagner, C. Mioskowski, Tetrahedron 2004, 60, 6807-6812.
23. M. Kimura, M. Fukasaka, Y. Tamaru, Synthesis 2006, 3611-3616.
24. K. Iikubo, Y. Ishikawa, N. Ando, K. Umezawa, S. Nishiyama, Tetrahedron Lett. 2002, 43, 291-293.
25. a) N. Kornblum, P. J. Berrigan, W. J. le Noble, J. Am. Chem. Soc. 1963, 85, 1141-1147;
26. b) N. Kornblum, R. Seltzer, P. Haberfield, J. Am. Chem. Soc. 1963, 85, 1148-1154.
27. a) R. Breslow, Acc. Chem. Res. 2004, 37, 471-478;
28. b) R. Breslow, K. Groves, M. U. Mayer, J. Am. Chem. Soc. 2002, 124, 3622-3635.
29. M. C. Pirrung, Chem. Eur. J. 2006, 12, 1312-1317.
30. a) S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb, K. B. Sharpless, Angew. Chem. Int. Ed. 2005, 44, 3275-3279;
31. b) K. C. Nicolaou, H. Xu, M. Wartmann, Angew. Chem. Int. Ed. 2005, 44, 756-761.
32. K.-W. Rosenmund, H. Bach, Chem. Ber. 1961, 94, 2394-2400.
33. H. Schick, H. Schwarz, A. Finger, S. Schwarz, Tetrahedron 1982, 38, 1279-1283.
34. C. M. A. de Oliveira, A. M. Porto, V. Bittrich, I. Vencato, A. J. Marsaioli, Tetrahedron Lett. 1996, 37, 6427-6430.
35. R. A. Hussain, A. G. Owegby, P. Parimoo, P. G. Watermann, Planta Med. 1982, 42, 78-81.
36. A. L. M. Porto, S. M. F. Machado, C. M. A. de Oliveira, V. Bittrich, M. do C. E. Amaral, A. J. Marsaioli, Phytochemistry 2000, 55, 755-768.
37. a) V. P. Pathak, R. N. Khanna, Indian J. Chem., Sect. B 1982, 21, 253-254;
38. b) M. Mondal, V. G. Puranik, N. P. Argade, J. Org. Chem. 2007, 72, 2068-2076.
39. a) R. Stevens, Chem. Rev. 1967, 67, 19-71;
40. b) L. Verotta, Phytochem. Rev. 2002, 1, 389-407.
41. E. H. Evans, A. T. Hewson, L. A. March, I. W. Nowell, A. H. Wadsworth, J. Chem. Soc. Perkin Trans. 1 1987, 127-149.
42. a) K. C. Nicolaou, J. A. Pfefferkorn, S. Kim, H. X. Wei, J. Am. Chem. Soc. 1999, 121, 4724-4725;
43. b) K. C. Nicolaou, J. A. Pfefferkorn, G.-Q. Cao, S. Kim, J. Kessabi, Org. Lett. 1999, 1, 807-810.
44. D. R. Siegel, S. J. Danishefsky, J. Am. Chem. Soc. 2006, 128, 1048-1049.
45. For a review, see: M. T. Reetz, Angew. Chem. Int. Ed. Engl. 1982, 21, 96-108.
46. For example, see: a) T. Pei, R. A. Widenhoefer, J. Am. Chem. Soc. 2001, 123, 11290-11291;
47. b) D. Yang, J.-H. Li, Q. Gao, Y.-L. Yan, Org. Lett. 2003, 5, 2869-2871.
48. K. C. Nicolaou, T. Montagnon, G. Vassilikogiannakis, J. Am. Chem. Soc. 2005, 127, 8872-8888.