Skip to main content
SpringerLink
Log in

Total synthesis of norneolignans fromKrameria species

  • Research Article
  • Article
  • Published:
Archives of Pharmacal Research Aims and scope Submit manuscript

Abstract

The total synthesis of norneolignans isolated fromKrameria species, 2-aryl-5-(E)-propenylben-zofurans (5, 11), is described. The key step involves the one-pot reaction fbr 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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • 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 nomeolignans fromKrameria cystisoides.Phytochemistry, 26, 1159–1166 (1987a).

    Article  CAS  Google Scholar 

  • Achenbach, H., Gross, J., Dominguez, X. A., Star J. V., and Salgado, F., Ramosissin and othermethoxylated nomeolignans fromKrameria Ramosissima.Phytochemistry, 26, 2041–2043 (1987b).

    Article  CAS  Google Scholar 

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

    Google Scholar 

  • Bohme, H. and Krack, W., α-Chloroalkylsulfides and sulfoniumsalze.Ann. Chem., 51–69 (1977).

  • Choi, H. D., Seo, P. J., and Son, B. W., Synthesis of 2-arylbenzo[b]furan derivatives from substituted phenols.J. Kor. Chem. Soc., 43, 606–608 (1999).

    CAS  Google Scholar 

  • Choi, H. D., Seo, P. J., and Son, B. W., Total synthesis of a norneolignan fromRatanhia radix.Arch. Pharm. Res., 25, 786–788 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Donnelly, D. M. X., Finet, J. P. and Kielty, J. M., Synthesis of a norneolignan fromKrameria Ramosissima.Tetrahedron Lett., 32, 3835–3836 (1991).

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    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. Kor. Chem. Soc., 44, 391–394 (2000).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Pukyong National University, 608-737, Busan, Korea

    Byeng-Wha Son

  2. Department of Chemistry, Dongeui University, 614-714, Busan, Korea

    Pil-Ja Seo, Hong-Dae Choi & Byeng-Wha Son

Authors
  1. Pil-Ja Seo
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hong-Dae Choi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Byeng-Wha Son
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Pil-Ja Seo.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Seo, PJ., Choi, HD. & Son, BW. Total synthesis of norneolignans fromKrameria species. Arch Pharm Res 27, 1189–1193 (2004). https://doi.org/10.1007/BF02975879

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02975879

Key words

Search

Navigation