Microwave-enhanced synthesis of new (-)-steganacin and (-)-steganone aza analogues / Beryozkina T., Appukkuttan P., Mont N., Van Der Eycken E. // Organic Letters. - 2006. - V. 8, l. 3. - P. 487-490.

ISSN:
15237060
Type:
Article
Abstract:
A novel, microwave-enhanced, highly efficient protocol for the synthesis of hitherto unknown (-)-steganacin and (-)-steganone 7-aza analogues containing a 1,2,3-triazole ring has been presented. Microwave irradiation was found to be highly beneficial in promoting the Suzuki reaction and the 1,3-dipolar cycloaddition reaction to generate the highly strained medium-sized ring system of the title molecules. © 2006 American Chemical Society.
Author keywords:
Index keywords:
drug derivative; gamma butyrolactone; heterocyclic compound; lignan; steganacin; steganone; triazole derivative; article; chemical structure; chemistry; cyclization; microwave radiation; stereoisomeri
DOI:
10.1021/ol052766f
Смотреть в Scopus:
https://www.scopus.com/inward/record.uri?eid=2-s2.0-32644441797&doi=10.1021%2fol052766f&partnerID=40&md5=51248fb0482b99d53b50666d004c381d
Соавторы в МНС:
Другие поля
Поле Значение
Link https://www.scopus.com/inward/record.uri?eid=2-s2.0-32644441797&doi=10.1021%2fol052766f&partnerID=40&md5=51248fb0482b99d53b50666d004c381d
Affiliations Department of Chemistry, University of Leuven, Celestijnenlaan 200F, B-3001 Heverlee, Belgium
Chemicals/CAS gamma butyrolactone, 96-48-0; steganacin, 41451-68-7; steganone, 41451-70-1; 4-Butyrolactone, 96-48-0; Aza Compounds; Lignans; steganacin, 41451-68-7; steganone; Triazoles
References Kupchan, S.M., Britton, R.W., Ziegler, M.F., Gilmore, Ch.J., Restivo, R.J., Bryan, R.F., (1973) J. Am. Chem. Soc., 95, pp. 1335-1336; Wang, R.W., Rebhum, L.I., Kupchan, S.M., (1977) Cancer Res., 37, pp. 3071-3079; Sackett, D.L., (1993) Pharmacol. Ther., 59, pp. 163-228; Zavala, F., Guenard, D., Robin, J.-P., Brown, E., (1980) J. Med. Chem., 23, pp. 546-549; Tomioka, K., Kubota, Y., Kawasaki, H., Koga, K., (1989) Tetrahedron Lett., 30, pp. 2949-2952; Kubota, Y., Kawasaki, H., Tomioka, K., Koga, K., (1993) Tetrahedron, 49, pp. 3081-3090; Dhal, R., Landais, Y., Lebrun, A., Lenain, V., Robin, J.P., (1994) Tetrahedron, 50, pp. 1153-1164; Stang, P.J., Zhdankin, V.V., (1996) Chem. Rev., 96, pp. 1123-1178; Tohma, H., Kita, Y., (2003) Top. Curr. Chem., 224, pp. 209-248; Reddy, P.P., Chu, C.-Y., Hwang, D.-R., Wang, S.-K., Uang, B.-J., (2003) Coord. Chem. Rev., 237, pp. 257-269. , and references therein; Meyers, A.I., Flisak, J.R., Aitken, R.A., (1987) J. Am. Chem. Soc., 109, pp. 5446-5452; Magnus, P., Schultz, J., Gallagher, T., (1985) J. Am. Chem. Soc., 107, pp. 4984-4988; Monovich, L.G., Le Huerou, Y., Roenn, M., Molander, G.A., (2000) J. Am. Chem. Soc., 122, pp. 52-57; Kamikawa, K., Watanabe, T., Daimon, A., Uemura, M., (2000) Tetrahedron, 56, pp. 2325-2337; Appukkuttan, P., Orts, A.B., Chandran, R.P., Goeman, J.L., Van Der Eycken, J., Dehaen, W., Van Der Eycken, E., (2004) Eur. J. Org. Chem., pp. 3277-3285; Appukkuttan, P., Dehaen, W., Van Der Eycken, E., (2005) Org. Lett., 7, pp. 2723-2726; Miyaura, N., Suzuki, A., (1995) Chem. Rev., 95, pp. 2457-2483; Diederich, F., Stang, P.J., (1998) Metal-Catalyzed Cross-Coupling Reactions, p. 517. , Wiley-VCH: Weinheim; Suzuki, A.J., (1999) Organomet. Chem., 576, pp. 147-168; Kotha, S., Lahiri, K., Kashinath, D., (2002) Tetrahedron, 58, pp. 9633-9695. , and references therein; Leadbeater, N.E., (2005) Chem. Commun., 23, pp. 2881-2902; Apukkuttan, P., Van Der Eycken, E., Dehaen, W., (2005) Synlett, pp. 127-133; Punna, S., Diaz, D.D., Li, C., Sharpless, K.B., Fokin, V.V., Finn, M.G., (2004) Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.), 45, pp. 778-779; Kolb, H.C., Sharpless, K.B., (2003) Drug Discov. Today, 8, pp. 1128-1137; Kolb, H.C., Finn, M.G., Sharpless, K.B., (2001) Angew. Chem., Int. Edit., 40, pp. 2004-2021. , and references therein; Apukkuttan, P., Fokin, V.V., Dehaen, W., Van Der Eycken, E., (2004) Org. Lett., 6, pp. 4223-4225; Kaval, N., Ermolat'Ev, D., Appukkuttan, P., Dehaen, W., Kappe, C.O., Van Der Eycken, E., (2005) J. Comb. Chem., 7, pp. 490-502; Biagi, G., Calderone, V., Giorgi, I., Livi, O., Martinotti, E., Martelli, A., Nardi, A., (2004) Farmaco, 59, pp. 397-404; Su, C., Lee, L.-X., Yu, S.-H., Shih, Y.-K., Su, J.-C., Li, F.-J., Lai, C., (2004) Liq. Cryst., 31, pp. 745-749; Zhu, X., Schmidt, R.R., (2004) J. Org. Chem., 69, pp. 1081-1085; Olesen, P.H., Sorensen, A.R., Urso, B., Kurtzhals, P., Bowler, A.N., Ehrbar, U., Hansen, B.F., (2003) J. Med. Chem., 46, pp. 3333-3341; Lewis, W.G., Green, L.G., Grynszpan, F., Radic, Z., Carlier, P.R., Taylor, P., Finn, M.G., Sharpless, K.B., (2002) Angew. Chem., Int. Ed., 41, pp. 1053-1057. , and references therein; Rostovtsev, V.V., Green, L.G., Fokin, V.V., Sharpless, K.B., (2002) Angew. Chem., Int. Ed., 41, pp. 2596-2599; Wang, Q., Chan, T.R., Hilgraf, R., Fokin, V.V., Sharpless, K.B., Finn, M.G., (2003) J. Am. Chem. Soc., 125, pp. 3192-3193; Tornoe, C.W., Christensen, C., Meldal, M., (2002) J. Org. Chem., 67, pp. 3057-3064; (1984) 1,3-Dipolar Cycloaddition Chemistry, , Padwa, A.; Ed.; Wiley-Interscience: New York; Gothelf, K.V., Jørgensen, K.A., (1998) Chem. Rev., 98, pp. 863-909. , and references therein; L'Abbe, G., (1969) Chem. Rev., 69, pp. 345-363; Appel, R., (1975) Angew. Chem. Int. Ed. Engl., 14, pp. 801-811
Correspondence Address Van Der Eycken, E.; Department of Chemistry, University of Leuven, Celestijnenlaan 200F, B-3001 Heverlee, Belgium; email: erik.vandereycken@chem.kuleuven.be
PubMed ID 16435866
Language of Original Document English
Abbreviated Source Title Org. Lett.
Source Scopus