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À propos de : Total Synthesis of (15R)- and (15S)-F2t-Isoprostanes by aBiomimetic Process Using the Cyclization of AcyclicDihydroxylated Octa-5,7-dienyl Radicals        

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  • Total Synthesis of (15R)- and (15S)-F2t-Isoprostanes by aBiomimetic Process Using the Cyclization of AcyclicDihydroxylated Octa-5,7-dienyl Radicals
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  • We report a new route to F2t-IsoP (formerly named 8-epi-PGF2α) using a biomimetic radicalcyclization of a highly functionalized C20 precursor. The strategy employed gives a β-hydroxy freeradical followed by molecular oxygen trapping, which is an unusual method for quenching carbonfree radicals. We observed the formation of unique diastereoisomers (15R)- and (15S)-F2t-IsoP. Thisresult is consistent with a strong stereoelectronic control associated with a steric effect initiatedby the side chains α and ω on the cyclopentane ring.
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