Diastereoselective elaboration of 2,3,4-substituted piperidines using diene iron tricarbonyl complexes. Total synthesis of (+/-)-dienomycin C and (+/-)-4-epi-dienomycin C

被引：18

作者：

Ripoche, I ^{[1
]}

Bennis, K ^{[1
]}

Canet, JL ^{[1
]}

Gelas, J ^{[1
]}

Troin, Y ^{[1
]}

机构：

[1] UNIV CLERMONT FERRAND,ENSCCF,LAB CHIM HETEROCYCLES & GLUCIDES,F-63174 CLERMONT FERRAN,FRANCE

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 23期

关键词：

D O I：

10.1016/0040-4039(96)00621-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereoselective formation of 2,3,4-substituted piperidines is achieved by condensation of the iron dienal complex 2 and the primary amine 3 via an intramolecular Mannich-type cyclisation. This method is illustrated by the first total synthesis of (+/-)-dienomycin C 1 and its C-4 epimer 9. (C) 1996 Elsevier Science Ltd

引用

页码：3991 / 3992

页数：2

共 8 条

[1] A NOVEL SYNTHESIS OF 2-ARYL-4-PIPERIDONES BY MANNICH CYCLIZATION OF IMINOKETALS [J].

BOSCH, J ;

RUBIRALTA, M ;

MORAL, M ;

VALLS, M .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (03) :595-605

[2] CONFORMATIONAL ANALYSIS OF TRICARBONYL(DIENE)IRON COMPOUNDS [J].

CLINTON, NA ;

LILLYA, CP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (10) :3058-&

[3] SYNTHESIS FROM PREGNENOLONE OF FLUORESCENT CHOLESTEROL ANALOG PROBES WITH CONJUGATED UNSATURATION IN THE SIDE-CHAIN [J].

DREW, J ;

LETELLIER, M ;

MORAND, P ;

SZABO, AG .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4047-4052

[4]

RIPOCHE I, 1995, TETRAHEDRON LETT, V36, P6675, DOI 10.1016/00404-0399(50)1352-I

[5]

SEYDENPENNE J, 1988, REDUCTIONS ALUMINO B

[6] TRANSITION-METAL MEDIATED ASYMMETRIC-SYNTHESIS .15. DIRECTING GROUP COMPETITION IN ORGANOIRON INTERMEDIATES IN THE SYNTHESIS OF (+/-)-O-METHYLJOUBERTIAMINE [J].

STEPHENSON, GR ;

FINCH, H ;

OWEN, DA ;

SWANSON, S .

TETRAHEDRON, 1993, 49 (25) :5649-5662

[7] A NEW ANTIBIOTIC, DIENOMYCIN .1. SCREENING METHOD, ISOLATION AND CHEMICAL STUDIES [J].

UMEZAWA, S ;

TSUCHIYA, T ;

TATSUTA, K ;

HORIUCHI, Y ;

USUI, T .

JOURNAL OF ANTIBIOTICS, 1970, 23 (01) :20-&

[8] STUDIES ON DIENOMYCINS .2. CHEMICAL STRUCTURES OF DIENOMYCIN-A, DIENOMYCIN-B AND DIENOMYCIN-C [J].

UMEZAWA, S ;

TATSUTA, K ;

HORIUCHI, Y ;

TSUCHIYA, T ;

UMEZAWA, H .

JOURNAL OF ANTIBIOTICS, 1970, 23 (01) :28-&

← 1 →