Synthesis of C-1 indol-3-yl substituted tetrahydroisoquinoline derivatives via a Pictet-Spengler approach

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Abstract

A protocol for the diastereoselective synthesis of C-1 indol-3-yl substituted tetrahydroisoquinoline derivatives via Pictet-Spengler condensation with L-DOPA or L-DOPA derivatives and 1H-indole-3-carbaldehydes is presented. The protocol is used for the successful synthesis of several tetrahydroisoquinolines as well as diketopiperazine fused analogues. (C) 2012 Elsevier Ltd. All rights reserved.

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Subject classification (UKÄ) – MANDATORY

  • Chemical Sciences

Keywords

  • Pictet-Spengler condensation, L-DOPA, 1H-Indole-3-carbaldehydes, C-1, Indolyl tetrahydroisoquinolines, Diketopiperazine fused, tetrahydroisoquinolines
Original languageEnglish
Pages (from-to)4966-4970
JournalTetrahedron Letters
Volume53
Issue number37
Publication statusPublished - 2012
Publication categoryResearch
Peer-reviewedYes