Archives of Pharmacal Research

  • 제27권12호
  • /
  • Pages.1189-1193
  • /
  • 2004
  • /
  • 0253-6269(pISSN)
  • /
  • 1976-3786(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

Total Synthesis of Norneolignans from Krameria Species

  • 발행 : 2004.01.01
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

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.

키워드

참고문헌

  1. 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) https://doi.org/10.1016/S0031-9422(00)82370-5
  2. 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) https://doi.org/10.1016/S0031-9422(00)81754-9
  3. 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)
  4. Bohme, H. and Krack, W., $\alpha$-Chloroalkylsulfides and sulfoniumsalze. Ann. Chem., 51-69(1977) https://doi.org/10.1002/jlac.197719770108
  5. 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)
  6. 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) https://doi.org/10.1007/BF02976992
  7. Donnelly, D., M. X., Finet, J. P. and Kielty, J. M., Synthesis of a norneolignan from Krameria Ramosissima. Tetrahedron Lett., 32, 3835-3836(1991) https://doi.org/10.1016/S0040-4039(00)79388-9
  8. Lutjens, H. and Scammells, P. J., Synthesis of natural products possessing a benzo[b]furan Skeleton. Tetrahedron Lett., 39, 6581-6584 (1998) https://doi.org/10.1016/S0040-4039(98)01371-9
  9. Schreiber, F. G. and Stevenson, A., Synthesis of benzofuran Styrax extractives. J. Chem. Soc. Perkin Trans I, 1514-1518 (1976)
  10. 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)