Abstract
(Z)-Tetracos-5-enoic acid is a key intermediate in the biosynthesis of myocobacterial mycolic acids. Recently the methyl ester of its cyclopropene analogue, methyl 4-(2-octadecylcyclopropen-1- yl)butanoate, was shown to act as an inhibitor of mycolic acid biosynthesis. The related analogues methyl 5-(2-octadecylcyclopropen-1-yl)pentanoate and methyl 3-(2-octadecylcyclopropen-1-yl)propanoate have been synthesized, as well as the related cyclopropane esters methyl (Z)-4-(2-octadecylcyclopropan-1-yl)butanoate and methyl (Z)-5-(2-octadecylcyclopropan-1-yl)pentanoate. The synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate involved protection of the cyclopropene ring by iodination to allow oxidation of an alcohol to a carboxylic acid; the diiodocyclopropane was deprotected by a new mild procedure using activated zinc.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclopentanes
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Cyclopropanes / chemical synthesis*
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Cyclopropanes / chemistry*
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Cyclopropanes / pharmacology
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Fatty Acids, Nonesterified / chemical synthesis*
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Fatty Acids, Nonesterified / chemistry
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Fatty Acids, Nonesterified / pharmacology
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Indicators and Reagents
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Magnetic Resonance Spectroscopy
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Mass Spectrometry
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Molecular Structure
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Mycobacterium / drug effects
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Mycobacterium / metabolism
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Mycolic Acids / antagonists & inhibitors
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Mycolic Acids / metabolism*
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Propionates / chemical synthesis*
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Propionates / chemistry
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Propionates / pharmacology
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Valerates / chemistry*
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Valerates / pharmacology
Substances
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Cyclopentanes
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Cyclopropanes
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Fatty Acids, Nonesterified
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Indicators and Reagents
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Mycolic Acids
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Propionates
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Valerates
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methyl 3-(2-octadecylcyclopropen--1-yl)pentanoate
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methyl 3-(2-octadecylcyclopropen-1-yl)propanoate