The synthesis of (+)-nemorensic acid

被引：21

作者：

Donohoe, TJ

Guillermin, JB

Frampton, C

Walter, DS

机构：

[1] Roche Discovery Welwyn, Dept Chem, Welwyn Garden City AL7 3AY, Herts, England

[2] Univ Manchester, Dept Chem, Manchester M13 9PL, Lancs, England

来源：

CHEMICAL COMMUNICATIONS | 2000年 / 06期

关键词：

D O I：

10.1039/b000565g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of (+)-nemorensic acid in nine steps is described; key steps in the route were the stereoselective Birch reduction of a substituted furan, and addition of allyltrimethylsilane to an oxonium ion at C-5; an X-ray crystal structure of (-)-nemorensic acid provided proof of the relative stereochemistry of the target.

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收藏

页码：465 / 466

页数：2

相关论文

共 12 条

[1] DIASTEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED TETRAHYDROFURAN DERIVATIVES FROM GAMMA-LACTOLS [J].

BRUCKNER, C ;

LOREY, H ;

REISSIG, HU .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (06) :556-557

[2]

DILLON MP, 1995, J CHEM SOC CHEM COMM, P1645

[3] The synthesis of (-)-cis- and (-)-trans-crobarbatic acid [J].

Donohoe, TJ ;

Stevenson, CA ;

Helliwell, M ;

Irshad, R ;

Ladduwahetty, T .

TETRAHEDRON-ASYMMETRY, 1999, 10 (07) :1315-1322

[4] Stereoselectivity in the birch reduction of 2-furoic acid derivatives [J].

Donohoe, TJ ;

Helliwell, M ;

Stevenson, CA ;

Ladduwahetty, T .

TETRAHEDRON LETTERS, 1998, 39 (19) :3071-3074

[5] Enantiospecific synthesis of (+)-nemorensic acid, a necic acid component of the macropyrrolizidine alkaloid, nemorensine [J].

Honda, T ;

Ishikawa, F .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (15) :5542-5546

[6] PYRROLIZIDINE ALKALOIDS .20. NEMORENSINE, AN ALKALOID FROM SENECIO-NEMORENSIS L [J].

KLASEK, A ;

SEDMERA, P ;

BOEVA, A ;

SANTAVY, F .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1973, 38 (08) :2504-2512

[7]

KLEIN LL, 1985, J AM CHEM SOC, V107, P257

[8] TITANIUM-MEDIATED CARBONYL OLEFINATIONS .1. METHYLENATIONS OF CARBONYL-COMPOUNDS WITH DIMETHYLTITANOCENE [J].

PETASIS, NA ;

BZOWEJ, EI .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (17) :6392-6394

[9] PYRROLIZIDINE ALKALOIDS [J].

ROBINS, DJ .

NATURAL PRODUCT REPORTS, 1995, 12 (04) :413-418

[10] [5+2] pyrone-alkene cycloaddition approach to tetrahydrofurans.: Expeditious synthesis of (±)-nemorensic acid [J].

Rodríguez, JR ;

Rumbo, A ;

Castedo, L ;

Mascareñas, JL .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (12) :4560-4563