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