Synthesis of analogues of Eunicea gamma-cembranolides containing cyclic ethers via saponification.
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.
Rodríguez
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Department of Chemistry, University of Puerto Rico, P.O. Box 23346, U.P.R. Station, San Juan, Puerto Rico 00931-3346. arodrig@goliath.cnnet.clu.edu
Piña
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Acosta
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Ramírez
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Soto
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D000818:Animals; D003063:Cnidaria / Q000737:chemistry*; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D004354:Drug Screening Assays, Antitumor; D004987:Ethers / Q000737:chemistry*; D006801:Humans; D013057:Spectrum Analysis; D014407:Tumor Cells, Cultured
D004224:Diterpenes; D004987:Ethers