Abstract
Addition of hydroxylamine to substituted 4-chlorobutanals gives intermediate nitrones that undergo tandem cyclization and then intramolecular dipolar cycloaddition to give the core ring system of the yuzurimine-type natural products. Ring-opening of the isoxazolidines gives amino alcohols that can be converted to 1,3-oxazines, representing the tetracyclic core of alkaloids such as daphcalycic acid and daphcalycine.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Aldehydes / chemistry*
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Alkaloids / chemical synthesis*
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Alkaloids / chemistry*
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Amino Alcohols / chemistry*
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Cyclization
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Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
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Heterocyclic Compounds, 4 or More Rings / chemistry*
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Molecular Structure
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Oxazines / chemical synthesis*
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Oxazines / chemistry*
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Stereoisomerism
Substances
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Aldehydes
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Alkaloids
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Amino Alcohols
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Heterocyclic Compounds, 4 or More Rings
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Oxazines
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daphcalycine