Total synthesis of (±)-clivonine via Diels-Alder reactions of 3,5-dibromo-2-pyrone.
JOURNAL OF ORGANIC CHEMISTRY(2020)
摘要
New synthetic routes to (+/-)-clivonine were devised starting with the Diels-Alder cycloadditions of 3,5-dibromo-2-pyrone with styrene pinacol boronate dienophiles. In the first-generation synthesis, the pivotal perhydroindoline system including the CS-hydroxyl group was constructed via a reaction sequence involving the Eschenmoser-Claisen rearrangement and regio/stereoselective epoxide opening reaction. In the second-generation synthesis, a radical-mediated cyclization approach was employed for the rapid assembly of the pyrrolidine ring. In this route, the C5-hydroxyl group provided by the dienophile in a stereochemically defined form was preserved throughout the synthesis.
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关键词
total synthesis,diels–alder reactions
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