research article

Synthesis of L-3-hydroxy-4-methoxy-5-methylphenylalanol

Demoulin, Nicolas
•
Zhu, Jieping  
2009
Synlett

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)]

Type
research article
DOI
10.1055/s-0028-1087548
Author(s)
Demoulin, Nicolas
Zhu, Jieping  
Date Issued

2009

Published in
Synlett
Issue

3

Start page

466

End page

468

Subjects

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)

Editorial or Peer reviewed

REVIEWED

Written at

OTHER

EPFL units
LSPN  
Available on Infoscience
November 25, 2010
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/58406