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The trivial name plakortolide F was claimed simultaneously by Hamann (ref 5d) and Wright (ref 4d) for two peroxide-lactones isolated from distinct Plakinastrella sponge species. The compound herein referred to as plakortolide F (i. e., 5) was identical to the material reported by the Wright group
-
The trivial name plakortolide F was claimed simultaneously by Hamann (ref 5d) and Wright (ref 4d) for two peroxide-lactones isolated from distinct Plakinastrella sponge species. The compound herein referred to as plakortolide F (i. e., 5) was identical to the material reported by the Wright group.
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24
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77958572061
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37Rv at concentrations ≥ 64 μg/mL
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37Rv at concentrations ≥ 64 μg/mL.
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For related peroxide-lactones having trans methyl substituents at the C-4 and C-6 positions, see refs 5b and 5d
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For related peroxide-lactones having trans methyl substituents at the C-4 and C-6 positions, see refs 5b and 5d.
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The lowest value for ΔΔδ in the article by Kishi and coworkers (ref 9a) is -0.029
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The lowest value for ΔΔδ in the article by Kishi and coworkers (ref 9a) is -0.029.
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31
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77958606041
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The conjugated polyene chain of compounds 1, 2, and 4 is a reactive, electron-rich system that is likely susceptible to attack by electrophilic reagents such as hydroxy and peroxy radicals and thus is responsible for the instability of these compounds toward oxidation
-
The conjugated polyene chain of compounds 1, 2, and 4 is a reactive, electron-rich system that is likely susceptible to attack by electrophilic reagents such as hydroxy and peroxy radicals and thus is responsible for the instability of these compounds toward oxidation.
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32
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77958580962
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Given their extreme chemical instability, we speculate that Nature uses unsaturated conjugated polyenes such as 1, 2, and 4 as biogenetic precursors to the phenyl polyketide peroxide series of Plakortis / Plakinastrella metabolites (i.e., the plakortolides) via a cascade of efficient E / Z -isomerizations, electrocyclizations, and further dehydrogenations to account for aromatic ring formation. For articles suggesting that some of these conversions are chemically viable, see
-
Given their extreme chemical instability, we speculate that Nature uses unsaturated conjugated polyenes such as 1, 2, and 4 as biogenetic precursors to the phenyl polyketide peroxide series of Plakortis / Plakinastrella metabolites (i.e., the plakortolides) via a cascade of efficient E / Z -isomerizations, electrocyclizations, and further dehydrogenations to account for aromatic ring formation. For articles suggesting that some of these conversions are chemically viable, see
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77958564088
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Wright and co-workers reported that free acid 4 showed moderate antifungal activity against Candida albicans, whereas 5 was inactive against both C. albicans and Aspergillus fumigatus; see ref 4d
-
Wright and co-workers reported that free acid 4 showed moderate antifungal activity against Candida albicans, whereas 5 was inactive against both C. albicans and Aspergillus fumigatus; see ref 4d.
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36
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77958611941
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-
In order to obtain reliable results, it is essential that both R - and S -enantiomers of the shift reagent be of similar quality (purity and moisture content) and that NMR data with both the R - and S -shift reagent be collected on the same instrument
-
In order to obtain reliable results, it is essential that both R-and S -enantiomers of the shift reagent be of similar quality (purity and moisture content) and that NMR data with both the R-and S -shift reagent be collected on the same instrument.
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37
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77958587720
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13C NMR chemical shifts assigned to the carbonyl carbons of 3 are not very accurate, as these signals were weak and broad. The assignments shown can be interchanged
-
13C NMR chemical shifts assigned to the carbonyl carbons of 3 are not very accurate, as these signals were weak and broad. The assignments shown can be interchanged.
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38
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77958517182
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It has been noted that Δδ are always greater with chiral Pr-based shift reagents than with the corresponding Eu-based shift reagents. Thus, the former lanthanide shift reagents have a superior capacity for enantiotopic discrimination of carbons within a molecule; see ref 9a
-
It has been noted that Δδ are always greater with chiral Pr-based shift reagents than with the corresponding Eu-based shift reagents. Thus, the former lanthanide shift reagents have a superior capacity for enantiotopic discrimination of carbons within a molecule; see ref 9a.
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