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A General Methodology for the Enantioselective Synthesis of 1‐Substituted Tetrahydroisoquinoline Alkaloids
Author(s) -
Amat Mercedes,
Elias Viviane,
Llor Núria,
Subrizi Fabiana,
Molins Elies,
Bosch Joan
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000473
Subject(s) - chemistry , enantioselective synthesis , enantiopure drug , tetrahydroisoquinoline , tricyclic , stereoselectivity , reagent , alkaloid , aryl , grignard reagent , stereochemistry , alkyl , lactam , combinatorial chemistry , organic chemistry , catalysis
Starting from tricyclic lactam 2 , which is easily accessible by cyclocondensation of δ‐oxoester 1 with ( R )‐phenylglycinol, a three‐step synthetic route to enantiopure 1‐substituted tetrahydroisoquinolines, including 1‐alkyl‐, 1‐aryl‐, and 1‐benzyltetrahydroisoquinoline alkaloids, as well as the tricyclic alkaloid (–)‐crispine A, has been developed. The key step is a stereoselective α‐amidoalkylation reaction using the appropriate Grignard reagent.
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