Abstract
The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(II), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Animals
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Antifungal Agents / chemical synthesis*
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Antifungal Agents / chemistry
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Antifungal Agents / pharmacology
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Antineoplastic Agents, Phytogenic / chemical synthesis*
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / pharmacology
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Catalysis
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Chromatography
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Colonic Neoplasms
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Diterpenes / chemistry*
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Drug Screening Assays, Antitumor
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry
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Heterocyclic Compounds, 4 or More Rings / pharmacology
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Humans
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Inhibitory Concentration 50
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Juniperus / chemistry*
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Leukemia P388
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Lung Neoplasms
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Magnetic Resonance Spectroscopy
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Melanoma
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Mice
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Molecular Structure
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Oxidation-Reduction
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Plants, Medicinal / chemistry*
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Stereoisomerism
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Structure-Activity Relationship
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Temperature
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Tumor Cells, Cultured / drug effects
Substances
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Antifungal Agents
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Antineoplastic Agents, Phytogenic
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Diterpenes
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Heterocyclic Compounds, 4 or More Rings
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communic acid
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oidiolactone C