Synthetic studies towards the phloroglucin natural product hyperforin: construction of the fully prenylated bicyclic core

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3519-3522

  Mehta, Goverdhan ^a   Bera, Mrinal K ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

HYPERFORIN; PHLOROGLUCINOL; PRENYLAMINE;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; PRENYLATION; STEREOCHEMISTRY;

EID: 65549170142     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.041     Document Type: Article

References (32)

1. Review:. Ciochina R., and Grossman R.B. Chem. Rev. 106 (2006) 3963-3986
2. Selected references: Early work,. Karanjgoakar C.G., Rama Rao A.V., Venkataraman K., and Palmer K.J. Tetrahedron Lett. 14 (1973) 4977-4980
3. Baystrov N.S., Chernov B.K., Dobrynin V.N., and Kolosov M.N. Tetrahedron Lett. 16 (1975) 2791-2794
4. More recently,. Šavikin-Fodulović K., Aljančić I., Vajs V., Menković N., Macura S., Gojgić G., and Milosavljević S. J. Nat. Prod. 66 (2003) 1236-1238
5. Lin Y.L., and Wu Y.S. Helv. Chim. Acta 86 (2003) 2156-2162
6. Wu J., Cheng X.-F., Harrison L.J., Goh S.-H., and Sim K.-Y. Tetrahedron Lett. 45 (2004) 9657-9659
7. Verotta L., Lovaglio E., Sterner O., Appendino G., and Bombardelli E. J. Org. Chem. 69 (2004) 7869-7874
8. Weng J.-R., Tsao L.-T., Wang J.-P., Wu R.-R., and Lin C.-N. J. Nat. Prod. 67 (2004) 1796-1799
9. Wu C.-C., Weng J.-R., Won S.-J., and Lin C.-N. J. Nat. Prod. 68 (2005) 1125-1127
10. Herath K., Jayasuriya H., Ondeyka J.G., Guan Z., Borris R.P., Stijfhoorn E., Stevenson D., Wang J., Sharma N., Macnaul K., Menke J.G., Ali A., Schulman M.J., and Singh S.B. J. Nat. Prod. 68 (2005) 617-619
11. Baggett S., Protiva P., Mazzola E.P., Yang H., Ressler E.T., Basile M.J., Weinstein I.B., and Kennelly E.J. J. Nat. Prod. 68 (2005) 354-360
12. Massoit G., Long C., David B., Serrano M.J., Daubie F., Alby F., Ausseil F., Knibiehler M., Moretti C., Hoffmann J.S., Cazaux C., and Lavaud C. J. Nat. Prod. 68 (2005) 979-984
13. Hernandez I.M., Fernandez M.C., Cuesta-Rubio O., Piccinelli A.N., and Rastrelli L. J. Nat. Prod. 68 (2005) 931-934
14. Taher M., Idris M.S., Ahmad F., and Arbain D. Phytochemistry 66 (2005) 723-726
15. Cao S., Brodie P.J., Miller J.S., Ratovoson F., Birkinshaw C., Randrianasolo S., Rakotobe E., Rasamison V.E., and Kingston D.G.I. J. Nat. Prod. 70 (2007) 686-688
16. For a recent review on the bioactivity of hyperforin, see:. Medina M.A., Martinez-Poveda B., Amores-Sanchez M.I., and Quesada A.R. Life. Sci. 79 (2006) 105-111
17. Chatterjee S.S., Bhattacharya S.K., Wonnemann M., Singer A., and Muller W.E. Life. Sci. 63 (1998) 499-510
18. Moore L.B., Goodwin B., Jones S.A., Wisely G.B., Cosette J., Singh S., Wilson T.M., Collins J.L., and Kliewers S.A. Proc. Natl. Acad. Sci. U.S.A. 97 (2000) 7500-7502
19. Muller W.E., Singer A., and Wonnemann M. Pharmacopsychiatry 34 (2001) S98-102
20. Mennini T., and Gobi M. Life. Sci. 75 (2004) 1021-1027
21. Schempp C.M., Pelz K., Wittmer A., Schopf E., and Simon J.C. Lancet 353 (1999) 2129
22. Verotta L., Appendino G., Bombardelli E., and Brun R. Bioorg. Med. Chem. Lett. 17 (2007) 1544-1548
23. Gey C., Kyrylenko S., Hennig L., Nguyen L.-H.D., Buttner A., Pham H.D., and Giannis A. Angew. Chem., Int. Ed. 46 (2007) 5219-5222
24. Mehta G., and Bera M.K. Tetrahedron Lett. 49 (2008) 1417-1420
25. Nicolaou K.C., Carenzi G.E.A., and Jeso V. Angew. Chem., Int. Ed. 44 (2005) 3895-3899
26. Shimizu Y., Kuramochi A., Usuda H., Kanai M., and Shibasaki M. Tetrahedron Lett. 48 (2007) 4173-4177
27. Abe M., and Nakada M. Tetrahedron Lett. 48 (2007) 4873-4877 and references cited therein
28. Mehta G., and Bera M.K. Tetrahedron Lett. 47 (2006) 689-692
29. Mehta G., Bera M.K., and Chatterjee S. Tetrahedron Lett. 49 (2008) 1121-1124
30. See also:. Usuda H., Kanai M., and Shibasaki M. Org. Lett. 4 (2002) 859-862
31. 2 (M+Na): 407.2926, found: 407.2926.
32. Gheorghe A., Schulte M., and Reiser O. J. Org. Chem. 71 (2006) 2173-2177