Abstract
An attempt to prepare a trimer having the 1,3,5-trioxazatriquinane skeleton led to discovery of a novel rearrangement reaction that afforded a compound with an oxabicyclo[3.2.1]octane skeleton whose reaction mechanism was proposed. On the basis of this mechanism, we synthesized the rearranged product from a dimethyl acetal intermediate in excellent yield. The compound with an oxabicyclo[3.2.1]octane skeleton showed high affinity for mu and kappa but not delta opioid receptor types. The compound expected to be a key intermediate for novel kappa selective ligands.
MeSH terms
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Acetals / chemistry
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Analgesics, Opioid / chemical synthesis*
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Chemistry, Organic / methods
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Chemistry, Pharmaceutical / methods*
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Drug Design
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Kinetics
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Ligands
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Models, Chemical
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Molecular Conformation
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Morphinans / chemistry
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Morphine / chemistry
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Receptors, Opioid, delta / chemistry
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Receptors, Opioid, kappa / agonists*
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Receptors, Opioid, kappa / chemistry
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Receptors, Opioid, mu / chemistry
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Spiro Compounds / chemistry
Substances
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Acetals
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Analgesics, Opioid
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Ligands
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Morphinans
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Receptors, Opioid, delta
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Receptors, Opioid, kappa
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Receptors, Opioid, mu
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Spiro Compounds
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TRK 820
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Morphine