Synthesis of the proposed structure of plakevulin A: revised structure of plakevulin A

[Display omitted] A total synthesis of the proposed structure of plakevulin A was accomplished. However, the NMR spectral data of the synthetic plakevulin A were not identical of those of the reported compound. We next converted the synthetic plakevulin A into 1-dihydrountenone A. The 1H and 13C NMR...

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Bibliographic Details
Published inTetrahedron letters Vol. 45; no. 43; pp. 8069 - 8071
Main Authors Saito, Fumiyo, Takeuchi, Ryo, Kamino, Tomoyuki, Kuramochi, Kouji, Sugawara, Fumio, Sakaguchi, Kengo, Kobayashi, Susumu, Tsuda, Masashi, Kobayashi, Jun’ichi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 18.10.2004
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
UNTENONE-A
CYCLOPENTENONE
INHIBITORS
DNA-POLYMERASE-ALPHA
(-)-UNTENONE-A
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Summary:[Display omitted] A total synthesis of the proposed structure of plakevulin A was accomplished. However, the NMR spectral data of the synthetic plakevulin A were not identical of those of the reported compound. We next converted the synthetic plakevulin A into 1-dihydrountenone A. The 1H and 13C NMR spectral data of 1-dihydrountenone A were identical with those of reported plakevulin A except for the peaks derived from levulinic acid. Thus, we repurified sample of the natural product and confirmed that the natural sample contained 1-dihydrountenone A and levulinic acid in the ratio of one to one. We also found that not plakevulin A but 1-dihydountenone A possessed the inhibitory activity against mammalian DNA polymerases α and β.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2004.08.173