Abstract
[reaction: see text] The first synthesis of (-)-dysiherbaine has been accomplished using intramolecular SN2 substitutions of a carbamate anion on an epoxide and an alkoxide on a secondary mesylate to efficiently construct the bicyclic skeleton stereospecifically from xylose. A general sequence has been developed to introduce an allyl group and convert it to the alanine side chain that should be useful for the construction of dysiherbaine analogues.
Publication types
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Alanine* / analogs & derivatives*
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Amino Acids / chemical synthesis*
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Amino Acids / chemistry
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Bridged Bicyclo Compounds, Heterocyclic*
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Heterocyclic Compounds, 2-Ring / chemical synthesis*
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Heterocyclic Compounds, 2-Ring / chemistry
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Hydrolysis
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Magnetic Resonance Spectroscopy
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Stereoisomerism
Substances
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Amino Acids
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Bridged Bicyclo Compounds, Heterocyclic
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Heterocyclic Compounds, 2-Ring
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dysiherbaine
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Alanine