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

被引：44

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

共 57 条

[1]

Allef P, 2007, HETEROCYCLES, V74, P421

[2] A new asymmetric synthesis of the anti-tumor alkaloid (R)-(+)-Crispine A [J].

Allin, Steven M. ;

Gaskell, Sean N. ;

Towler, Joannah M. R. ;

Page, Philip C. Bulman ;

Saha, Basu ;

McKenzie, Michael J. ;

Martin, William P. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (23) :8972-8975

[3] Stereoselective α-amidoalkylation reactions of phenylglycinol-derived bicyclic lactams [J].

Amat, M ;

Escolano, C ;

Llor, N ;

Huguet, M ;

Pérez, M ;

Bosch, J .

TETRAHEDRON-ASYMMETRY, 2003, 14 (12) :1679-1683

[4] Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam [J].

Amat, M ;

Llor, N ;

Hidalgo, J ;

Escolano, C ;

Bosch, J .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) :1919-1928

[5] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine [J].

Amat, M ;

Bosch, J ;

Hidalgo, J ;

Cantó, M ;

Pérez, M ;

Llor, N ;

Molins, E ;

Miravitlles, C ;

Orozco, M ;

Luque, J .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) :3074-3084

[6] A biomimetic enantioselective approach to the decahydroquinoline class of dendrobatid alkaloids [J].

Amat, Mercedes ;

Griera, Rosa ;

Tabregat, Robert ;

Molins, Elies ;

Bosch, Joan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (18) :3348-3351

[7] Straightforward methodology for the enantioselective synthesis of benzo[a]- and indolo[2,3-a]quinolizidines [J].

Amat, Mercedes ;

Santos, Maria M. M. ;

Bassas, Oriol ;

Llor, Nuria ;

Escolano, Carmen ;

Gomez-Esque, Arantxa ;

Molins, Elies ;

Allin, Steven M. ;

McKee, Vickie ;

Bosch, Joan .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (14) :5193-5201

[8] Dynamic kinetic resolution and desymmetrization processes:: A straightforward methodology for the enantioselective synthesis of piperidines [J].

Amat, Mercedes ;

Bassas, Oriol ;

Llor, Nuria ;

Canto, Margalida ;

Perez, Maria ;

Molins, Elies ;

Bosch, Joan .

CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (30) :7872-7881

[9] Stereoselective α-amidoalkylation of phenylglycinol-derives lactams.: Synthesis of enantiopure 5,6-disubstituted 2-piperidones [J].

Amat, Mercedes ;

Escolano, Carmen ;

Gomez-Esque, Arantxa ;

Lozano, Oscar ;

Llor, Nuria ;

Griera, Rosa ;

Molins, Efies ;

Bosch, Joan .

TETRAHEDRON-ASYMMETRY, 2006, 17 (10) :1581-1588

[10] First Enantioselective Synthesis of the Diazatricyclic Core of Madangamine Alkaloids [J].

Amat, Mercedes ;

Perez, Maria ;

Proto, Stefano ;

Gatti, Teresa ;

Bosch, Joan .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (31) :9438-9441

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