Novel synthesis of heterocycles having a functionalized carbon center via nickel-mediated carboxylation: Total synthesis of erythrocarine

被引：97

作者：

Shimizu, K ^{[1
]}

Takimoto, M ^{[1
]}

Mori, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 13期

关键词：

D O I：

10.1021/ol034670w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Novel synthetic procedure of heterocycles was developed using nickel-mediated alkylative carboxylation, and the total synthesis of erythrocarine was achieved using this method and RCM of dienyne as the key steps.

引用

页码：2323 / 2325

页数：3

共 27 条

[1] CARBON-DIOXIDE AS AN ALTERNATIVE C1 SYNTHETIC UNIT - ACTIVATION BY TRANSITION-METAL COMPLEXES [J].

BEHR, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (05) :661-678

[2] REACTIONS OF CARBON-DIOXIDE WITH CARBON CARBON BOND FORMATION CATALYZED BY TRANSITION-METAL COMPLEXES [J].

BRAUNSTEIN, P ;

MATT, D ;

NOBEL, D .

CHEMICAL REVIEWS, 1988, 88 (05) :747-764

[3] ERYTHRINA ALKALOIDS .8. ALKALOIDS IN SEEDS OF 4 ERYTHRINA SPECIES [J].

CHAWLA, AS ;

REDHA, FMJ ;

JACKSON, AH .

PHYTOCHEMISTRY, 1985, 24 (08) :1821-1823

[4] FROM STOICHIOMETRY TO CATALYSIS - ELECTROREDUCTIVE COUPLING OF ALKYNES AND CARBON-DIOXIDE WITH NICKEL BIPYRIDINE COMPLEXES - MAGNESIUM-IONS AS THE KEY FOR CATALYSIS [J].

DERIEN, S ;

DUNACH, E ;

PERICHON, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8447-8454

[5]

Dyke S.F., 1981, ALKALOIDS CHEM PHYSL, V18, P1, DOI DOI 10.1016/S1876-0813(08)60236-5

[6] Erythrina alkaloids VII Isolation and characterization of the new alkaloids, erythraline and erythratine [J].

Folkers, K ;

Koniuszy, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :436-441

[7] CATALYTIC RING-CLOSING METATHESIS OF FUNCTIONALIZED DIENES BY A RUTHENIUM CARBENE COMPLEX [J].

FU, GC ;

NGUYEN, ST ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (21) :9856-9857

[8] The organometallic chemistry of carbon dioxide [J].

Gibson, DH .

CHEMICAL REVIEWS, 1996, 96 (06) :2063-2095

[9]

GROTJAHN DB, 1993, SYNTHESIS-STUTTGART, P579

[10]

HILL RK, 1967, ALKALOIDS, V9, P281

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