Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Total Synthesis of a Norneolignan from Ratanhia Radix

  • Published : 2002.12.01
Download PDF
⟨ Previous Next ⟩

Abstract

The total synthesis of a norneolignan isolated from Ratanhia, 5-(3-hydroxypropyl)-2-(2'-methoxy-4'-hydroxyphenyl)benzofuran (8), is described. The key steps contain the one-pot reaction for a 2-arylbenzofuran 6 from methyl 3-(4-hydroxyphenyl)propionate with 2-chloro-2-methylthio-(2'-methoxy-4'-acetoxy)acetophenone (5) in the presence of $ZnCl_2$, and reductive desulfurization of the resulting product 6.

Keywords

References

  1. Arnone, P., Di Modugno, V., Nasini, G. and Venturini, I., Isolation and structure determination of new active neolignans and ncrneolignans from Ratanhia. Gazz. Chim. Ital., 118, 675.682 (1988)
  2. Bohme, H-. and Krack, W, a-Chloroalkylsulfide and -sulfonium-salze. Ann. Chem., 51 (1977)
  3. Choi, H. D., Ha, M. C., Seo, P. J., Son, B. Wand Song, J. C., Total synthesis of a demethoxy-egonol from Styrax obassia. Arch. Pharm. Res., 23, 438-440 (2000) https://doi.org/10.1007/BF02976567
  4. Choi, H. D., Seo, P. J. and Son, B. W., Synthesis of 2-arylbenzo[b]furan derivatives from substituted phenols. J. Korean Chem. Soc., 43, 606-608 (1999)
  5. Komatsu, M., Yokoe, I. and Shirataki, Y., Studies on the constituents of Sophora species. Chem. Pharm. Bull., 26, 1274-1278 (1978) https://doi.org/10.1248/cpb.26.1274
  6. Lutjens, H. and Scammells, P. J., Synthesis of natural products possessing a benzo[b]furan skeleton. Tetrahedron Letters, 39, 6581-6584 (1998) https://doi.org/10.1016/S0040-4039(98)01371-9
  7. Mooradian, A., Cavallito, C. Bergman, A. J. and Lawson, E. J., A new series of testosteron esters, J. Am. Chem. Soc., 71, 3372-3374 (1949) https://doi.org/10.1021/ja01178a030
  8. Schreiber, F. G. and Stevenson, R., Synthesis of benzofuran Styrax extractives. J. Chem. Soc., Perkin Trans., 1, 1514-1518 (1976)
  9. Seo, P. J., Ha, M. C., Choi, H. D. and Son, B. W., Synthesis of 2-(multimethoxyphenyl)benzo[b]furan derivatives from substituted phenols and application. J. Korean Chem. Soc., 44, 391-394 (2000)