Abstract
A chemoselective conversion of bastadin-4 to the important Ca2+ channel modulator bastadin-5 (1a) has been achieved using cationic hydrogenation (Et3SiH, TFA, 60%). Specifically deuterated bastadin-5 (1b, >95 at. %) was prepared following this method and the simplified 1H NMR H-5/H2-6 spin system of 1b exploited to study temperature-dependent macrocyclic ring dynamics.
Publication types
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Research Support, U.S. Gov't, Non-P.H.S.
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Research Support, U.S. Gov't, P.H.S.
MeSH terms
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Animals
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Calcium Channel Agonists / chemical synthesis*
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Calcium Channel Agonists / pharmacology
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Cyclization
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Halogenated Diphenyl Ethers
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Hydrogenation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Oxidation-Reduction
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Phenyl Ethers / chemical synthesis*
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Phenyl Ethers / chemistry*
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Phenyl Ethers / pharmacology
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Porifera / chemistry*
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Temperature
Substances
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Calcium Channel Agonists
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Halogenated Diphenyl Ethers
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Phenyl Ethers
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bastadin 4
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bastadin 5