Abstract
The total synthesis of the naturally occurring (Z)-2-methoxy-5-hexadecenoic acid and (Z)-2-methoxy-6-hexadecenoic acid was accomplished using as a key step Mukaiyama's trimethylsilyl cyanide addition to 4- and 5-pentadecenal, respectively. These syntheses further confirm the structures of the natural marine fatty acids and corroborate their cis double-bond stereochemistry. The title compounds were antimicrobial against the Gram-positive bacteria Staphylococcus aureus (MIC 0.35 micromol/mL) and Streptococcus faecalis (MIC 0.35 micromol/mL).
Publication types
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Research Support, Non-U.S. Gov't
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Anti-Bacterial Agents / chemical synthesis*
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Anti-Bacterial Agents / pharmacology
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Enterococcus faecalis / drug effects
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Fatty Acids, Monounsaturated / chemical synthesis*
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Fatty Acids, Monounsaturated / isolation & purification
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Gram-Negative Bacteria / drug effects*
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Magnetic Resonance Spectroscopy
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Microbial Sensitivity Tests
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Spectrophotometry, Infrared
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Staphylococcus aureus / drug effects
Substances
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2-methoxy-5-hexadecenoic acid
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2-methoxy-6-hexadecenoic acid
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Anti-Bacterial Agents
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Fatty Acids, Monounsaturated