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Concise syntheses of (+/-)-protoemetinol and related alkaloids using radical cyclisation

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JournalTetrahedron Letters
DatePublished - 16 Mar 2011
Issue number11
Volume52
Number of pages3
Pages (from-to)1154-1156
Original languageEnglish

Abstract

Both (+/-)-protoemetinol, its 3-epi-isomer and (+/-)-3-desmethyl protoemetinol have been prepared in five linear steps from a dihydroisoquinoline using a 6-exo-trig cyclisation of a vinyl radical in the key step. This novel and particularly short route has potential application in the synthesis of Alangium and Mitragyna alkaloids. (C) 2011 Elsevier Ltd. All rights reserved.

    Research areas

  • Alkaloid, Cyclisation, Radical, Tributyltin hydride, FORMAL TOTAL-SYNTHESIS, 1ST TOTAL-SYNTHESIS, INDOLE ALKALOIDS, MITRAGYNA-SPECIOSA, GENERAL-APPROACH, (-)-PROTOEMETINOL, PIPERIDINES, (+)-VELLOSIMINE, (-)-EMETINE, CHEMISTRY

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