Abstract
Four stereoisomers of the spider-pathogenic fungus metabolite torrubiellone D were synthesized for the first time in 10% overall yield starting from L-tyrosine or D-tyrosine. The 3-decatrienoyl side chain was assembled and attached via (E)-selective HWE and Wittig olefinations. Their antibiotic activities against drug-susceptible Escherichia coli strains differed considerably.
MeSH terms
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Alkaloids* / chemical synthesis
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Alkaloids* / chemistry
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Alkaloids* / isolation & purification
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Alkaloids* / pharmacology
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Animals
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Anti-Bacterial Agents* / chemical synthesis
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Anti-Bacterial Agents* / chemistry
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Anti-Bacterial Agents* / isolation & purification
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Anti-Bacterial Agents* / pharmacology
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Enterococcus faecium / drug effects
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Escherichia coli / drug effects
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Hypocreales / chemistry*
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Microbial Sensitivity Tests
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Molecular Structure
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Pyrrolidinones / chemistry
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Spiders / microbiology*
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Staphylococcus aureus / drug effects
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Stereoisomerism
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Tyrosine / chemistry
Substances
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Alkaloids
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Anti-Bacterial Agents
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Pyrrolidinones
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torrubiellone D
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Tyrosine
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tetramic acid