Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step

Fadila Louafi; Jean-Pierre Hurvois; Aïssa Chibani; Thierry Roisnel

doi:10.1021/jo100714y

Synthesis of tetrahydroisoquinoline alkaloids via anodic cyanation as the key step

J Org Chem. 2010 Aug 20;75(16):5721-4. doi: 10.1021/jo100714y.

Authors

Fadila Louafi¹, Jean-Pierre Hurvois, Aïssa Chibani, Thierry Roisnel

Affiliation

¹ Département de Chimie, Faculté des Sciences Exactes,Université Mentouri de Constantine, Route de Ain El Bey,25000 Constantine, Algérie.

PMID: 20704442
DOI: 10.1021/jo100714y

Abstract

We report a new route to tetrahydroisoquinoline (THIQ) alkaloids involving the alkylation of alpha-aminonitrile 2 as a key step. The latter compound was prepared by anodic cyanation of the corresponding tertiary amine 1. Reductive decyanation of alpha-aminonitriles 6a-c proceeded diastereoselectively (up to 95% de) to deliver the C1-substituted alkaloids precursors 9a-c. The syntheses of (+/-)-carnegine, (+/-)-norlaudanosine, and (+/-)-O,O-dimethylcoclaurine have been achieved.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkaloids / chemical synthesis*
Alkaloids / chemistry
Molecular Structure
Nitriles / chemistry*
Stereoisomerism
Tetrahydroisoquinolines / chemical synthesis*
Tetrahydroisoquinolines / chemistry

Substances

Alkaloids
Nitriles
Tetrahydroisoquinolines