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

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Research output: Contribution to journal › Article

Published copy (DOI)

10.1016/j.tetlet.2011.01.007

Author(s)

Matthew J. Palframan
Andrew F. Parsons
Paul Johnson

Department/unit(s)

Chemistry

Publication details

Journal	Tetrahedron Letters
Date	Published - 16 Mar 2011
Issue number	11
Volume	52
Number of pages	3
Pages (from-to)	1154-1156
Original language	English

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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