Synthesis of Analogues of Eunicea γ-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 a...

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Bibliographic Details
Published in:Journal of organic chemistry 2001-02, Vol.66 (3), p.648-658
Main Authors: Rodríguez, Abimael D, Piña, Ivette C, Acosta, Ana L, Ramírez, Catherine, Soto, Javier J
Format: Article
Language:English
Subjects:
Animals
Cnidaria - chemistry
Diterpenes - chemical synthesis
Diterpenes - chemistry
Drug Screening Assays, Antitumor
Ethers - chemistry
Humans
Spectrum Analysis
Tumor Cells, Cultured
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo001025j