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Total synthesis of a norneolignan fromratanhia radix

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Abstract

The total synthesis of a norneolignan isolated fromRatanhia, 5-(3-hydroxypropyl)-2-(2′-meth-oxy-4′-hydroxyphenyl) benzofuran (8), is described. The key steps contain the one-pot reaction for a 2-arylbenzofuran6 from methyl 3-(4-hydroxyphenyl)propionate with 2-chloro-2-meth-ylthio-(2′-methoxy-4′-acetoxy) acetophenone (5) in the presence of ZnCI2, and reductive des-ulfurization of the resulting product6.

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References

  • Amone, A., Di Modugno, V., Nasini, G. and Venturini, I., Isolation and structure determination of new active neolignans and norneolignans fro.Ratanhia. Gazz. Chim. Ital., 118, 675–682 (1988).

    Google Scholar 

  • Bohme, H. and Krack, W., α-Chloroalkylsulfide and-sulfonium-salze.Ann. Chem., 51 (1977).

  • Choi, H. D., Ha, M. C., Seo, P. J., Son, B. W. and Song, J. C., Total synthesis of a demethoxy-egonol fro.Styrax obassia. Arch. Pharm. Res., 23, 438–440 (2000).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    CAS  Google Scholar 

  • Komatsu, M., Yokoe, I. and Shirataki, Y., Studies on the constituents o.Sophora species.Chem. Pharm. Bull., 26, 1274–1278 (1978).

    CAS  Google Scholar 

  • Lutjens, H. and Scammells, P. J., Synthesis of natural products possessing a benzo[b]furan skeleton.Tetrahedron Letters, 39, 6581–6584 (1998).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Schreiber, F. G. and Stevenson, R., Synthesis of benzofuranStyrax extractives.J. Chem. Soc., Perkin Trans I, 1514–1518 (1976).

    Article  Google Scholar 

  • 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).

    CAS  Google Scholar 

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Correspondence to Hong -Dae Choi.

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Choi, H.D., Seo, P.J. & Son, B.W. Total synthesis of a norneolignan fromratanhia radix. Arch Pharm Res 25, 786–789 (2002). https://doi.org/10.1007/BF02976992

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  • DOI: https://doi.org/10.1007/BF02976992

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