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

页码：4017 / 4026

页数：10

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