Abstract
[reaction: see text] An enantioselective Diels-Alder reaction catalyzed by an Evans' copper-bis(oxazoline) complex was utilized to construct a highly functionalized spirolactam, a key intermediate in our projected total synthesis of the marine toxin, gymnodimine. Additional transformations, including a mild N-tosyl group deprotection, afforded a keto spirocyclic imine moiety, the proposed pharmacophore of gymnodimine. Thus, the prepared ketone is a potentially useful intermediate for conjugation to provide an immunogen for eventual monitoring of gymnodimine and congeners.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, Non-U.S. Gov't
MeSH terms
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Crystallography, X-Ray
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Heterocyclic Compounds, 3-Ring / chemical synthesis*
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Heterocyclic Compounds, 3-Ring / chemistry*
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Heterocyclic Compounds, 3-Ring / pharmacology
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Hydrocarbons, Cyclic / chemical synthesis*
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Hydrocarbons, Cyclic / chemistry*
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Hydrocarbons, Cyclic / pharmacology
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Imines / chemical synthesis*
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Imines / chemistry*
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Imines / pharmacology
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Marine Toxins / chemical synthesis*
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Marine Toxins / chemistry*
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Marine Toxins / pharmacology
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Molecular Conformation
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Molecular Structure
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Stereoisomerism
Substances
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Heterocyclic Compounds, 3-Ring
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Hydrocarbons, Cyclic
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Imines
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Marine Toxins
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gymnodimine