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Total Synthesis of the Ortho-Hydroxylated Protoberberines (S)-Govaniadine, (S)-Caseamine, and (S)-Clarkeanidine via a Solvent-Directed Pictet–Spengler Reaction

[Image: see text] The common para regioselectivity in Pictet–Spengler reactions with dopamine derivatives is redirected to the ortho position by a simple change of solvents. In combination with a chiral auxiliary on nitrogen, this ortho-selective Pictet–Spengler produced the 1-benzyltetrahydroisoqui...

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Detalhes bibliográficos
Publicado no:J Org Chem
Main Authors: Horst, Brendan, Wanner, Martin J., Jørgensen, Steen Ingemann, Hiemstra, Henk, van Maarseveen, Jan H.
Formato: Artigo
Idioma:Inglês
Publicado em: American Chemical Society 2018
Acesso em linha:https://ncbi.nlm.nih.gov/pmc/articles/PMC6328280/
https://ncbi.nlm.nih.gov/pubmed/30451502
https://ncbi.nlm.nih.govhttp://dx.doi.org/10.1021/acs.joc.8b02378
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