Divergent Total Synthesis Of The Natural Antimalarial Marinoquinolines A, B, C, E And Unnatural Analogues

A new synthetic route to marinoquinolines was developed, allowing the synthesis of several structurally related compounds from a common key intermediate. Four natural marinoquinolines (A, B, C and E) and nine unnatural new analogues were prepared by this strategy, which features a Heck-Matsuda reaction in pure water and the Pictet-Spengler reaction as key steps. © 2012 Elsevier Ltd. All rights reserved.533648364840Sangnoi, Y., Sakulkeo, O., Yuenyongsawad, S., Kanjana-Opas, A., Ingkaninan, K., Plubrukarn, A., Suwanborirux, K., (2008) Mar. Drugs, 6, p. 578Kanjana-Opas, A., Panphon, S., Fun, H.-K., Chantrapromma, S., (2006) Acta Cryst. e, 62, p. 2728Okanya, P.W., Mohr, K.I., Gerth, K., Jansen, R., Müller, R., (2011) J. Nat. Prod., 74, p. 603Li, S.-F., Di, Y.-T., He, H.-P., Zhang, Y., Wang, Y.-H., Yin, J.-L., Tan, C.-J., Hao, X.-J., (2011) Tetrahedron Lett., 52, p. 3186Carroll, A.R., Duffy, S., Avery, V.M., (2010) J. Org. Chem., 75, p. 8291Atkinson, C.M., Mattocks, A.R., (1957) J. Chem. Soc., p. 3722Parrick, J., Wilcox, R., (1976) J. Chem. Soc., Perkin Trans. 1, p. 2121Govindachari, T., Sudarsan, V., Rajappa, S., (1961) Tetrahedron, 16, p. 1Van Baelen, G., Lemiere, G.L.F., Dommisse, R.A., Maes, B.U.W., (2009) Arkivoc, p. 174Molina, P., Alajarin, M., Sanchezandrada, P., (1993) Synthesis, p. 225Ni, L., Li, Z., Wu, F., Xu, J., Wu, X., Kong, L., Yao, H., (2012) Tetrahedron Lett., 53, p. 1271Schwalm, C.S., De Castro, I.B.D., Ferrari, J., De Oliveira, F.L., Aparicio, R., Correia, C.R.D., (2012) Tetrahedron Lett., 53, p. 1660Roglans, A., Pla-Quintana, A., Moreno-Mañas, M., (2006) Chem. Rev., 106, p. 4622Taylor, J.G., Moro, A.V., Correia, C.R.D., (2011) Eur. J. Org. Chem., p. 1403Felpin, F.-X., Nassar-Hardy, L., Le Callonnec, F., Fouquet, E., (2011) Tetrahedron, 67, p. 2815De Oca, A., Correia, C.R.D., (2003) Arkivoc, p. 390Kundu, B., Sawant, D., Chhabra, R., (2005) J. Comb. Chem., 7, p. 317Duggineni, S., Sawant, D., Saha, B., Kundu, B., (2006) Tetrahedron, 62, p. 3228Sharma, S., Saha, B., Sawant, D., Kundu, B., (2007) J. Comb. Chem., 9, p. 783David, E., Pellet-Rostaing, E., Lemaire, M., (2007) Tetrahedron, 63, p. 8999Saha, B., Sharma, S., Sawant, D., Kundu, B., (2008) Tetrahedron, 64, p. 8676Agarwal, P.K., Sharma, S.K., Sawant, D., Kundu, B., (2009) Tetrahedron, 65, p. 1153Mandadapu, A.K., Saifuddin, M., Agarwal, P.K., Kundu, B., (2009) Org. Biomol. Chem., 7, p. 2796Sharma, S., Kundu, B., (2009) J. Comb. Chem., 11, p. 720Verma, A.K., Jha, R.R., Sankar, V.K., Aggarwal, T., Singh, R.P., Chandra, R., (2011) Eur. J. Org. Chem., p. 699