Organocatalytic enantioselective Pictet-Spengler approach to biologically relevant 1-benzyl-1,2,3,4-tetrahydroisoquinoline alkaloids.
J Org Chem
; 80(10): 5125-32, 2015 May 15.
Article
em En
| MEDLINE
| ID: mdl-25909585
ABSTRACT
A general procedure for the synthesis of 1-benzyl-1,2,3,4-tetrahydroisoquinolines was developed, based on organocatalytic, regio- and enantioselective Pictet-Spengler reactions (86-92% ee) of N-(o-nitrophenylsulfenyl)-2-arylethylamines with arylacetaldehydes. The presence of the o-nitrophenylsulfenyl group, together with the MOM-protection in the catechol part of the tetrahydroisoquinoline ring system, appeared to be a productive combination. To demonstrate the versatility of this approach, 10 biologically and pharmaceutically relevant alkaloids were prepared using (R)-TRIP as the chiral catalyst (R)-norcoclaurine, (R)-coclaurine, (R)-norreticuline, (R)-reticuline, (R)-trimemetoquinol, (R)-armepavine, (R)-norprotosinomenine, (R)-protosinomenine, (R)-laudanosine, and (R)-5-methoxylaudanosine.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Produtos Biológicos
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Benzilisoquinolinas
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Tetra-Hidroisoquinolinas
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Alcaloides
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Etilaminas
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Isoquinolinas
Idioma:
En
Ano de publicação:
2015
Tipo de documento:
Article