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(b) A reexamination of S. baconi, as reported by Garson (ref 1b), failed to detect any baconipyrones, such that they may conceivably be artifacts of the isolation process rather than biosynthetically related metabolites to the siphonarins. This may also hold for other polypropionates obtained from siphonariids, as with muamvatin (ref 6b) and the denticulatins (ref 6c).
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20
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0442330812
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note
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The double Swern oxidation was routinely performed by employing oxalyl chloride (5 equiv), DMSO (10 equiv), and triethylamine (15 equiv). After warming from -78 to -20°C. the reaction mixture was quenched with a mixture of anhydrous hexane/toluene (3:1), followed by filtration through Celite, to obtain spectroscopically pure diketone. Other procedures (Dess-Martin, TPAP) led to undesired cyclisations of mono-oxidized products.
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0442283766
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note
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This also avoided the presence of sulfur residues in the subsequent hydrogenolysis of the benzyl group, which proved to be problematic due to catalyst poisoning.
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30
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33748664603
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Yamaguchi, M.5
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35
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85088000647
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note
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D values for baconipyrone C are now also quite similar to that recorded for the normethyl compound, baconipyrone D (4).
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36
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Garson, M. J.; Jones, D. J.; Small, C. J.; Liang, J.; Clardy, J. Tetrahedron Lett. 1994, 35, 6921.
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