Abstract
[reaction: see text] A unified strategy for the divergent and stereocontrolled introduction of the (E)- and (Z)-enamide side-chains of oximidines I, II, and III, salicylihalamides A and B, lobatamides A and D, and CJ-12,950 is detailed. The synthesis relied on the copper-promoted C-N coupling of (E)- and (Z)-vinyl iodides with a protected maleimide hemiaminal followed by deprotection and reaction of the resulting (E)- or (Z)-enelactam hemiaminals with O-methylhydroxylamine or propylidenetriphenylphosphorane.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alkenes / chemical synthesis*
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Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
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Copper / chemistry
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Cyclization
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Epoxy Compounds / chemical synthesis*
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Indicators and Reagents
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Lactones / chemical synthesis*
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Macrolides / chemical synthesis*
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Models, Molecular
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Molecular Structure
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Salicylates / chemical synthesis*
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Stereoisomerism
Substances
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Alkenes
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Bridged Bicyclo Compounds, Heterocyclic
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CJ-12950
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Epoxy Compounds
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Indicators and Reagents
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Lactones
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Macrolides
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Salicylates
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lobatamide A
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lobatamide D
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oximidine I
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oximidine II
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oximidine III
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salicylihalamide A
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Copper