Synthesis of analogues of Eunicea gamma-cembranolides containing cyclic ethers via saponification

J Org Chem. 2001 Feb 9;66(3):648-58. doi: 10.1021/jo001025j.


A method for the synthesis of derivatives of the lead structures euniolide (1), 12,13-bisepieupalmerin (2), and eupalmerin acetate (3) containing tetrahydrofuran and tetrahydropyran ring systems was developed on the basis of alkali-induced intramolecular oxacyclizations. Representatives of the new analogues were submitted to the in vitro antitumor cell-line-screening program of the National Cancer Institute (NCI). While it was shown that a variety of structural modifications are possible, these transformations led typically to nontoxic synthetic cembranoids.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Cnidaria / chemistry*
  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry
  • Drug Screening Assays, Antitumor
  • Ethers / chemistry*
  • Humans
  • Spectrum Analysis
  • Tumor Cells, Cultured


  • Diterpenes
  • Ethers