Abstract
An asymmetric total synthesis of trilobacin (1), an annonaceous acetogenin with potent anticancer activities, was accomplished wherein the construction of its erythro-bis(2,2')-tetrahydrofuran core 2 featured a novel organoselenium-mediated oxonium ion formation/SiO(2)-promoted fragmentation of alpha,alpha'-cis-oxocene 3.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Cyclization
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Furans / chemical synthesis*
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Furans / chemistry
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Ions / chemistry
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Molecular Conformation
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Organoselenium Compounds / chemistry*
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Oxocins / chemistry*
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Silicon Dioxide / chemistry*
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Stereoisomerism
Substances
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Furans
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Ions
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Organoselenium Compounds
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Oxocins
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trilobacin
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Silicon Dioxide