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

TY - JOUR

T1 - Concise syntheses of (+/-)-protoemetinol and related alkaloids using radical cyclisation

AU - Palframan, Matthew J.

AU - Parsons, Andrew F.

AU - Johnson, Paul

PY - 2011/3/16

Y1 - 2011/3/16

N2 - 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.

AB - 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.

KW - Alkaloid

KW - Cyclisation

KW - Radical

KW - Tributyltin hydride

KW - FORMAL TOTAL-SYNTHESIS

KW - 1ST TOTAL-SYNTHESIS

KW - INDOLE ALKALOIDS

KW - MITRAGYNA-SPECIOSA

KW - GENERAL-APPROACH

KW - (-)-PROTOEMETINOL

KW - PIPERIDINES

KW - (+)-VELLOSIMINE

KW - (-)-EMETINE

KW - CHEMISTRY

UR - http://www.scopus.com/inward/record.url?scp=79751531889&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2011.01.007

DO - 10.1016/j.tetlet.2011.01.007

M3 - Article

SN - 0040-4039

VL - 52

SP - 1154

EP - 1156

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -