Browse > Article

Total Synthesis of Norneolignans from Krameria Species  

Seo , Pil-Ja (Department of Chemistry, Dongeui University)
Choi, Hong-Dae (Department of Chemistry, Dongeui University)
Son, Byeng-Wha (Department of Chemistry, Pukyong National University)
Publication Information
Archives of Pharmacal Research / v.27, no.12, 2004 , pp. 1189-1193 More about this Journal
Abstract
The total synthesis of norneolignans isolated from Krameria species, 2-aryl-5-(E)-propenylbenzofurans (5, 11), is described. The key step involves the one-pot reaction for 2-arylbenzofurans (2, 7) from 4-hydroxyphenylacetone with 4'-acetoxy-2-chloro-2-(methylthio)acetophenone (1) and 2-chloro-2-methylthio-(2',4',6'-trimethoxy)acetophenone (6) under Friedel-Crafts reactionconditions.
Keywords
Norneolignans; Krameria species; 2-ARYL-5-(E)-propenylbenzofurans; 4-Hydroxyphenylacetone; 4'-Acetoxy-2-chloro-2-(methlthio)acetophenone; 2-Chloro-2-methylthio-(2',4',6'-trimethoxy)acetophenone; FRiedel-Crafts reaction;
Citations & Related Records

Times Cited By Web Of Science : 2  (Related Records In Web of Science)
Times Cited By SCOPUS : 2
연도 인용수 순위
1 Achenbach, H., Gross, J., Dominguez, X. A., Star J. V., and Salgado, F., Ramosissin and othermethoxylated nomeolignans from Krameria Ramosissima. Phytochemistry, 26, 2041-2043 (1987b)   DOI   ScienceOn
2 Donnelly, D., M. X., Finet, J. P. and Kielty, J. M., Synthesis of a norneolignan from Krameria Ramosissima. Tetrahedron Lett., 32, 3835-3836(1991)   DOI   ScienceOn
3 Schreiber, F. G. and Stevenson, A., Synthesis of benzofuran Styrax extractives. J. Chem. Soc. Perkin Trans I, 1514-1518 (1976)
4 Seo, P. J., Ha, M. C., Choi, H. D., and Son, B. W., Synthesisof 2-(multimethoxyphenyl)benzo[b]furan derivatives from substitutedphenolsand application. J. Kor. Chem. Soc., 44, 391-394 (2000)
5 Choi, H. D., Seo, P. J., and Son, B. W., Total synthesis of a norneolignan from Ratanhia radix. Arch. Pharm. Res., 25, 786-788 (2002)   DOI   ScienceOn
6 Amone, A., Modugno, V., Nasini, G., and Venturini, I., Isolation and structure determination of new active neolignans and nomeolignans from Ratanhia. Gazz. Chim. Ital., 118, 675-682 (1988)
7 Lutjens, H. and Scammells, P. J., Synthesis of natural products possessing a benzo[b]furan Skeleton. Tetrahedron Lett., 39, 6581-6584 (1998)   DOI   ScienceOn
8 Bohme, H. and Krack, W., $\alpha$-Chloroalkylsulfides and sulfoniumsalze. Ann. Chem., 51-69(1977)   DOI
9 Choi, H. D., Seo, P. J., and Son, B. W., Synthesis of 2arylbenzo[b]furan derivatives from substituted phenols. J. Kor. Chem. Soc., 43, 606-608 (1999)
10 Achenbach, H., Gross, J., Dominguez, X. A., Cano, G., Star J. V., Brussolo, L. C., Munoz, G., Salgado, F., and Lopez L., Lignans, neolignans and norneolignans from Krameria cystisoides. Phytochemistry, 26, 1159-1166 (1987a)   DOI   ScienceOn