Heck Arylation Of Styrenes With Arenediazonium Salts: Short, Efficient, And Stereoselective Synthesis Of Resveratrol, Dmu-212, And Analogues

Short, efficient, and stereoselective synthesis of the trans-stilbenes resveratrol, DMU-212, and analogues of both compounds are described. The synthesis of these important anti-cancer agents feature the palladium catalyzed Heck-Matsuda arylation of styrenes with arenediazonium tetrafluoroborates. © 2008 Elsevier Ltd. All rights reserved.493956685671Renaud, S., De Lorgeril, M., (1992) Lancet, 339, p. 1523Baur, J.A., Pearson, K.J., Price, N.L., Jamieson, H.A., Lerin, C., Kalra, A., Prabhu, V.V., Sinclair, D.A., (2006) Nature, 444, p. 337Kimura, Y., Okuda, H., Arichi, S., (1985) Biochim. Biophys. Acta, 834, p. 275Inamori, Y., Kubo, M., Tsujibo, H., Ogawa, M., Saito, Y., Miki, Y., Takemura, S., (1987) Chem. Pharm. Bull., 35, p. 887Jang, D.S., Kang, B.S., Ryu, S.Y., Chang, I.M., Min, K.E., Kim, Y., (1999) Biochem. Pharmacol., 57, p. 705Chanvitayapongs, S., Draczynaka-Lusiak, B., Sun, A., (1997) Neuroreport, 8, p. 1499Mgbonnyebi, O., Russo, J., Russo, I., (1998) Int. J. Oncol., 12, p. 865Bhat, K.P., Lantvit, D., Christov, K., Mehta, R.G., Moon, R.C., Pezzuto, J.M., (2001) Cancer Res., 61, p. 7456Wang, Y., Lee, K.W., Chan, F.L., Chen, S., Leung, L.K., (2006) Toxicol. Sci., 92, p. 71Gupta, Y.K., Chaudhary, G., Srivastava, A.K., (2002) Pharmacology, 65, p. 170Doeherty, J.J., Fu, M.M.H., Stiffler, B.S., Limperos, R.J., Pokabla, C.M., DeLucia, A.L., (1999) Antiviral Res., 43, p. 145Stivala, L.A., Savio, M., Carafoli, F., Perucca, P., Bianchi, L., Maga, G., Forti, L., Vannini, V., (2001) J. Biol. Chem., 276, p. 22586Torres-Lopez, J.E., Ortiz, M.I., Castaneda-Hernandez, G., Alonso-Lopez, R., Asomoza-Espinosa, R., Grandos-Soto, V., (2002) Life Sci., 70, p. 1669Wang, Z.R., Huang, Y.Z., Zou, J.C., Cao, K.J., Xu, Y.N., Wu, J.M., (2002) Int. J. Mol. Med., 9, p. 77Sale, S., Verschoyle, R.D., Boocock, D., Jones, D.J.L., Wilsher, N., Ruparelia, K.C., Steward, W.P., Gescher, A.J., (2004) Br. J. Cancer, 90, p. 736Potter, G.A., Butler, P.C., Ruparelia, K.C., Ijaz, T., Wilsher, N., Wanogho, E., Tan, H.L., Burke, M.D., (2002) Br. J. Cancer, 86, pp. S117Sale, S., Tunstall, R.G., Ruparelia, K.C., Potter, G.A., Steward, W.P., Gescher, A.J., (2005) Int. J. Cancer, 115, p. 194Ferré-Filmon, K., Delaude, L., Demonceau, A., Noels, A.F., (2004) Coord. Chem. Rev., 248, p. 2323. , For a review on the synthesis of stilbenes, including resveratrol, see:Eddarir, S., Abdelhadi, Z., Rolando, C., (2001) Tetrahedron Lett., 42, p. 9127Yu, J., Gaunt, M.J., Spencer, J.B., (2002) J. Org. Chem., 67, p. 4627Guiso, M., Marra, C., Farina, A., (2002) Tetrahedron Lett., 43, p. 597Farina, A., Ferranti, C., Marra, C., (2006) Nat. Prod. Res., 20, p. 247Jeffery, T., Ferber, B., (2003) Tetrahedron Lett., 44, p. 193Andrus, M.B., Liu, J., Meredith, E.L., Nartey, E., (2003) Tetrahedron Lett., 44, p. 4819Botella, L., Nájera, C., (2004) Tetrahedron, 60, p. 5563Lebel, H., Ladjel, C., Bréthous, L., (2007) J. Am. Chem. Soc., 129, p. 13321Bazin, M.-A., Kihel, L.E., Lancelot, J.-C., Rault, S., (2007) Tetrahedron Lett., 48, p. 4347Ferre-Filmon, K., Delaude, L., Demonceau, A., Noels, A.F., (2005) Eur. J. Org. Chem., p. 3319Velder, J., Ritter, S., Lex, J., Schmalz, H.-G., (2006) Synthesis, p. 273Cross, G.G., Eisnor, C.R., Gossage, R.A., Jenkins, H.A., (2006) Tetrahedron Lett., 47, p. 2245Robinson, J.E., Taylor, R.J.K., (2007) Chem. Commun., p. 1617Roglans, A., Pla-Quintana, A., Moreno-Manas, M., (2006) Chem. Rev., 106, p. 4622. , For an excellent review, consult:Severino, E.A., Costenaro, E.R., Garcia, A.L.L., Correia, C.R.D., (2003) Org. Lett., 5, p. 305Meira, P.R.R., Moro, A.V., Correia, C.R.D., (2007) Synthesis, p. 2279Burtoloso, A.C.B., Garcia, A.L.L., Miranda, K.C., Correia, C.R.D., (2006) Synlett, p. 3145Pastre, J.C., Correia, C.R.D., (2006) Org. Lett., 8, p. 1657da Silva, K.P., Godoi, M.N., Correia, C.R.D., (2007) Org. Lett., 9, p. 2815Farina, A., Ferranti, C., Marra, C., Guiso, M., Norcia, G., (2007) Nat. Prod. Res., 21, p. 564Siegrist, U., Rapold, T., Blaser, H.-U., (2003) Org. Proc. Res. Dev., 7, p. 429. , The 3,4,5-trimethoxybenzenediazonium tetrafluoroborate was washed with a saturated aqueous solution sulfamic acid in order to destroy some residual sodium nitrite. This arenediazonium salt seems to perform at its best only after treatment with sulfamic acid( )Brooks, P.R., Wirtz, M.C., Vetelino, M.G., Rescek, D.M., Woodworth, G.F., Morgan, B.P., Coe, J.W., (1999) J. Org. Chem., 64, p. 971

Highly Regio- And Stereoselective Heck Reaction Of Allylic Esters With Arenediazonium Salts: Application To The Synthesis Of Kavalactones

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