A General Methodology for the Enantioselective Synthesis of 1-Substituted Tetrahydroisoquinoline Alkaloids

被引：43
|
作者：
Amat, Mercedes [1 ,2 ]
Elias, Viviane [1 ,2 ]
Llor, Nuria [1 ,2 ]
Subrizi, Fabiana [1 ,2 ]
Molins, Elies [3 ]
Bosch, Joan [1 ,2 ]
机构：
[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
[2] Univ Barcelona, Inst Biomed IBUB, E-08028 Barcelona, Spain
[3] Inst Ciencia Mat Barcelona, CSIC, Cerdanyola Del Valles 08193, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 21期
关键词：
Alkaloids; Heterocycles; Lactams; Asymmetric synthesis; Total synthesis; STEREOSELECTIVE ALPHA-AMIDOALKYLATION; ASYMMETRIC-SYNTHESIS; STRAIGHTFORWARD METHODOLOGY; BICYCLIC LACTAMS; CYCLIC IMINES; ISOQUINOLINE; (-)-SALSOLIDINE; HYDROGENATION; DERIVATIVES; PIPERIDINES;
D O I：
10.1002/ejoc.201000473
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Starting from tricyclic lactam 2, which is easily accessible by cyclocondensation of delta-oxoester 1 with (R)-phenylglycinol, a three-step synthetic route to enantiopure 1-substituted tetra-hydroisoquinolines, including 1-alkyl-, 1-aryl-, and 1-benzyl-tetrahydroisoquinoline alkaloids, as well as the tricyclic alkaloid (-)-crispine A, has been developed. The key step is a stereoselective alpha-amidoalkylation reaction using the appropriate Grignard reagent.
引用
收藏
页码：4017 / 4026
页数：10
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