Artículos de revistas
Total Synthesis Of (±)-homopumiliotoxin 223g
Registro en:
Tetrahedron Letters. , v. 42, n. 40, p. 6999 - 7001, 2001.
404039
10.1016/S0040-4039(01)01389-2
2-s2.0-0035479706
Autor
Santos L.S.
Pilli R.A.
Institución
Resumen
The total synthesis of (±)-homopumiliotoxin 223G was achieved in six steps and 14% yield through the addition of 5-methyl-2-triisopropylsilyoxyfuran (3) to the N-acyliminium ion derived from N-Cbz 2-methoxypiperidine featuring bicyclic lactam 9b as the key intermediate. © 2001 Elsevier Science Ltd. All rights reserved. 42 40 6999 7001 Daly, J.W., Garrafo, H.M., Spande, T.F., (1993) The Alkaloids, p. 85. , Cordell, G. A., Ed. San Diego, CA: Academic Press Daly, J.W., (1998) J. Nat. Prod., 61, p. 162 Jones, T.H., Gorman, J.S.T., Snelling, R.R., Delabie, J.H.C., Blum, M.S., Garraffo, H.M., Jain, P., Spande, T.F., (1999) J. Chem. Ecol., 25, p. 1179 Aoyagi, S., Hasegawa, Y., Hirashima, S., Kibayashi, C., (1998) Tetrahedron Lett., 39, p. 2149 Kibayashi, C., Aoyagi, S., Wang, T.C., Saito, K., Daly, J.W., Spande, T.F., (2000) J. Nat. Prod., 63, p. 1157 De Oliveira, M.C.F., Santos, L.S., Pilli, R.A., (2001) Tetrahedron Lett., 42, p. 6995 Santos, L.S., Pilli, R.A., (2000) 22nd IUPAC International Symposium on the Chemistry of Natural Products, , OSA-12, São Carlos, SP, Brazil Arend, M., Westermann, B., Risch, N., (1998) Angew. Chem., Int. Ed. Engl., 37, p. 1045 Nasman, H., Pensar, K.G., (1985) Synthesis, p. 786 Martin, S.F., Bur, S.K., (1999) Tetrahedron, 55, p. 8905 Morimoto, Y., Nishida, K., Hayashi, Y., Shirahama, H., (1993) Tetrahedron Lett., 34, p. 5773 noteFox, D.N.A., Lathbury, D., Mahon, M.F., Molloy, K.C., Gallagher, T., (1991) J. Am. Chem. Soc., 113, p. 2652 Stork, G., Shiner, C.S., Winkler, J.D., (1982) J. Am. Chem. Soc., 104, p. 310 Crabb, T.A., Newton, R.F., Jackson, D., (1971) Chem. Rev., 71, p. 109 Thornton, E.R., Stormes, M.N., (1991) J. Org. Chem., 56, p. 2489 Tokuyama, T., Nishimori, N., Shimada, A., (1987) Tetrahedron, 43, p. 643 Yoon, N.M., Brown, H.C., (1968) J. Am. Chem. Soc., 90, p. 2927