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| - Utility of Polymer-Supported Reagents in the Total Synthesis ofLamellarins
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| - Four solid-supported reagents have been utilized in the multistep synthesis of lamellarins. Theuse of Amberlyst A-26 Br3- and polymer bound pyridine hydrobromide perbromide (PVPHP) forketo α-bromination of the less studied ortho-substituted acetophenone derivatives selectivelyfurnished the corresponding monobromination products (phenacyl bromide derivatives), which wereused directly in condensation reactions with benzyldihydroisoquinoline mediated by Amberlyst A-26NaCO3-. The 2H-pyrrole carbonates subsequently underwent intramolecular Friedel−Craftstransacylation followed by lactonization to provide the lamellarin skeleton. Alternatively, AmberlystA-26 NaCO3- effectively served as base in condensation reaction of benzyldihydroisoquinoline withα-nitrocinnamate derivatives to provide the corresponding 2-ethoxycarbonyl pyrroles, whichsmoothly underwent O-debenzylation reaction followed by lactonization to furnish the lamellarinskeleton. The novel Amberlyst-15 mediated lactonization reactions effectively combined theotherwise two separate steps into a single transformation.
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