Asymmetric synthesis of protoberberine alkaloids via a tandem nucleophilic addition and intramolecular cyclisation of a chiral o-toluamide anion with 3,4-dihydroisoquinoline

被引：20

作者：

Warrener, RN

Liu, LG

Russell, RA

机构：

[1] Centre for Molecular Architecture, Central Queensland University, Rockhampton

来源：

CHEMICAL COMMUNICATIONS | 1997年 / 22期

关键词：

D O I：

10.1039/a706008d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The reaction of o-toluamide anions, derived from the (S)-(-)- and (R)-(+)-1-phenylethylamine, with 6, 7-dimethoxy-3, 4-dihydroisoquinoline gives (13aS)-(-)- and (13aR)-(+)-8-oxoprotoberberine, respectively, with enantiomeric excesses > 96%.

引用

页码：2173 / 2174

页数：2

共 22 条

[1]

[Anonymous], [No title captured]

[2]

BHAKUNI DS, 1986, ALKALOIDS, V28, P95

[3] SYNTHESIS OF 3-SUBSTITUTED AND 3,4-DISUBSTITUTED 3,4-DIHYDRO-1(2H)-ISOQUINOLONES BY CONDENSATION OF LITHIATED N,N-DIETHYL-ORTHO-TOLUAMIDE WITH IMINES [J].

CLARK, RD ;

JAHANGIR .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5378-5382

[4]

CZARNOCKI Z, 1992, J CHEM RES-S, P334

[5]

CZARNOCKI Z, 1986, B SOC CHIM BELG, V95, P749

[6] STEREOSPECIFIC CYCLIZATIONS OF IMINIUM SALTS FROM ALPHA-AMINO-ACID DECARBONYLATION - SYNTHESIS OF 8-METHYLBERBINES AND 13-METHYLBERBINES [J].

DEAN, RT ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4183-4189

[7] An efficient asymmetric synthesis of allo- and pseudo-7,8-dimethoxyberbane systems through tin-mediated three component coupling [J].

Haraguchi, Y ;

Kozima, S ;

Yamaguchi, R .

TETRAHEDRON-ASYMMETRY, 1996, 7 (02) :443-449

[8]

IWASA, 1981, HETEROCYCLES, V16, P901

[9] THE ABSOLUTE-CONFIGURATIONS OF (+)-THALICTRIFOLINE AND (+)-CORYDALIC ACID METHYL-ESTER - TOTAL SYNTHESIS OF (+)-THALICTRIFOLINE [J].

IWASA, K ;

GUPTA, YP ;

CUSHMAN, M .

TETRAHEDRON LETTERS, 1981, 22 (25) :2333-2336

[10] IMINIUM SALTS FROM ALPHA-AMINO-ACID DECARBONYLATION - APPLICATION TO THE SYNTHESIS OF OCTAHYDROINDOLO[2,3-A]QUINOLIZINES [J].

JOHANSEN, JE ;

CHRISTIE, BD ;

RAPOPORT, H .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (24) :4914-4920

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