Controlling stereoselectivity by enzymatic and chemical means to access enantiomerically pure (1S,3R)-1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline derivatives

Authors
Orden, Alejandro Agustin; Schrittwieser, Joerg H.; Resch, Verena; Mutti, Francesco G.; Kroutil, Wolfgang
Publication Year
2013
Language
English
Format
article
Status
Published version
Description
A chemoenzymatic strategy for the synthesis of enantiomerically pure novel alkaloids (1S,3R)- 1-benzyl-2,3-dimethyl-1,2,3,4-tetrahydroisoquinolines is presented. The key steps are the biocatalytic stereoselective reductive amination of substituted 1-phenylpropan-2-one derivatives to yield chiral amines employing microbial x-transaminases, and the diastereoselective reduction of a Bischler– Napieralski imine intermediate by catalytic hydrogenation in the presence of palladium on charcoal, leading exclusively to the desired cis-isomer
Fil: Orden, Alejandro Agustin. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina;
Fil: Schrittwieser, Joerg H.. University of Graz. Department of Chemistry, Organic and Bioorganic Chemistry; Austria;
Fil: Resch, Verena. University of Graz. Department of Chemistry, Organic and Bioorganic Chemistry; Austria;
Fil: Mutti, Francesco G.. University of Graz. Department of Chemistry, Organic and Bioorganic Chemistry; Austria;
Fil: Kroutil, Wolfgang. University of Graz. Department of Chemistry, Organic and Bioorganic Chemistry; Austria;
Subject
CHEMOENZYMATIC
ALKALOIDS
TRANSAMINASES
STEREOSELECTIVITY
Química Orgánica
Ciencias Químicas
CIENCIAS NATURALES Y EXACTAS
Access level
Open access
License
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repository
CONICET Digital (CONICET)
Institution
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identifier
oai:ri.conicet.gov.ar:11336/2208