AN EFFICIENT ROUTE TO CHIRAL TRANS-2,5-DIALKYLPYRROLIDINES VIA STEREOSELECTIVE INTRAMOLECULAR AMIDOMERCURATION

被引：45

作者：

TAKAHATA, H

TAKEHARA, H

OHKUBO, N

MOMOSE, T

机构：

[1] Faculty of Pharmaceutical Sciences, Toyama Medical and Pharmaceutical University, Toyama, 930-01

来源：

TETRAHEDRON-ASYMMETRY | 1990年 / 1卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(00)80547-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

An intramolecular amidomercuration of α-butylated 4-pentenylcarbamate 5 predominantly provided trans-2,5-disubstituted pyrrolidine 6, which was elaborated to chiral trans-5-butyl-2-alkylpyrrolidines 10 and 13, constituents of ant venoms. © 1990.

引用

页码：561 / 566

页数：6

共 24 条

[1] ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING [J].

ARSENIYADIS, S ;

HUANG, PQ ;

PIVETEAU, D ;

HUSSON, HP .

TETRAHEDRON, 1988, 44 (09) :2457-2470

[2] REDUCTION OF 2,5-DIALKYLPYRROLINES - A KEY STEP IN A SYNTHESIS OF NATURAL INSECTICIDES [J].

BACOS, D ;

CELERIER, JP ;

MARX, E ;

SALIOU, C ;

LHOMMET, G .

TETRAHEDRON LETTERS, 1989, 30 (09) :1081-1082

[3]

BACVALL JE, 1990, J ORG CHEM, V55, P826

[4]

Bartlett P. A., 1984, ASYMMETRIC SYNTHESIS, V3, P411

[5] ALKALOIDAL VENOM MACE - OFFENSIVE USE BY A THIEF ANT [J].

BLUM, MS ;

JONES, TH ;

HOLLDOBLER, B ;

FALES, HM ;

JAOUNI, T .

NATURWISSENSCHAFTEN, 1980, 67 (03) :144-145

[6] STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].

CARDILLO, G ;

ORENA, M .

TETRAHEDRON, 1990, 46 (10) :3321-3408

[7]

Coppola GM, 1987, ASYMMETRIC SYNTHESIS

[8] ALKALOIDS FROM DENDROBATID FROGS - STRUCTURES OF 2 OMEGA-HYDROXY CONGENERS OF 3-BUTYL-5-PROPYLINDOLIZIDINE AND OCCURRENCE OF 2,5-DISUBSTITUTED PYRROLIDINES AND A 2,6-DISUBSTITUTED PIPERIDINE [J].

DALY, JW ;

SPANDE, TF ;

WHITTAKER, N ;

HIGHET, RJ ;

FEIGL, D ;

NISHIMORI, N ;

TOKUYAMA, T ;

MYERS, CW .

JOURNAL OF NATURAL PRODUCTS, 1986, 49 (02) :265-280

[9] SYNTHESIS OF (+/-)-TRANS-2,5-DIALKYLPYRROLIDINES FROM THE LUKES-SORM DILACTAM - EFFICIENT PREPARATION OF (+/-)-TRANS-2-BUTYL-5-HEPTYLPYRROLIDINE AND ANALOGS PRESENT IN ANT VENOMS [J].

GESSNER, W ;

TAKAHASHI, K ;

BROSSI, A ;

KOWALSKI, M ;

KALINER, MA .

HELVETICA CHIMICA ACTA, 1987, 70 (08) :2003-2010

[10] STEREOSELECTIVITY IN INTRAMOLECULAR AMIDOMERCURATION - KINETIC VS THERMODYNAMIC CONTROL [J].

HARDING, KE ;

MARMAN, TH .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2838-2840

← 1 2 3 →