Résumé
The L-3-hydroxy-4-methoxy-5-methylphenylalanol, a common subunit of ecteinascidin and safracin family alkaloids, was synthesized from L-tyrosine in eight steps with an overall yield of 50%. [on SciFinder (R)]
Détails
Titre
Synthesis of L-3-hydroxy-4-methoxy-5-methylphenylalanol
Auteur(s)
Demoulin, Nicolas ; Zhu, Jieping
Publié dans
Synlett
Numéro
3
Pages
466-468
Date
2009
ISSN
0936-5214
Mots-clés (libres)
Coupling reaction (Suzuki-Miyaura; prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis); Baeyer-Villiger oxidation; Friedel-Crafts reaction; Hydrogenolysis; Methylation (prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis); Alkaloids Role: SPN (Synthetic preparation); PREP (Preparation) (prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis); tyrosine Friedel Crafts acylation; acetyl tyrosine prepn iodination; iodo acetyl tyrosine prepn Suzuki Miyaura methylation; methyl acetyl tyrosine prepn Baeyer Villiger oxidn; acetoxy tyrosine methyl prepn hydrogenolysis; hydroxy methoxy methyl phenylalanol prepn
Note
CAN 150:515329
31-2
Alkaloids
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
60-18-4 (L-Tyrosine); 13139-17-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis); 262360-92-9P; 851915-13-4P; 1150635-46-3P; 1150635-53-2P; 1150635-56-5P; 1150635-60-1P; 1150635-61-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis); 686776-27-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis)
31-2
Alkaloids
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
60-18-4 (L-Tyrosine); 13139-17-8 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis); 262360-92-9P; 851915-13-4P; 1150635-46-3P; 1150635-53-2P; 1150635-56-5P; 1150635-60-1P; 1150635-61-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis); 686776-27-2P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of hydroxy-methoxy-methylphenylalanol starting from L-tyrosine via Friedel-Crafts acylation-methylation-Suzuki-Miyaura coupling reaction-Baeyer-Villiger oxidn.-hydrogenolysis)
Laboratoires
LSPN
Le document apparaît dans
Production scientifique et compétences > SB - Faculté des sciences de base > ISIC - Institut des sciences et ingénierie chimiques > LSPN - Laboratoire de synthèse et produits naturels
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Travail hors EPFL
Articles de journaux
Publié
Publications validées par des pairs
Travail hors EPFL
Articles de journaux
Publié
Date de création de la notice
2010-11-25