Nickel powder promoted 5-endo radical cyclisations.: A concise approach to Erythrina alkaloids

被引：57

作者：

Cassayre, J

Quiclet-Sire, B

Saunier, JB

Zard, SZ ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

[2] Ecole Polytech, CNRS, Organ Synth Lab, F-91128 Palaiseau, France

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 49期

关键词：

D O I：

10.1016/S0040-4039(98)02036-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Alkenyl trichloroacetamides 3 undergo, upon refluxing with nickel powder and acetic acid in 2-propanol, exclusive 5-endo-trig cyclisation to afford functionalised lactams 4; these are attractive precursors of erythrina alkaloids, as demonstrated by-the expedient synthesis of 3-demethoxyerythratidinone 5. (C) 1998 Published by Elsevier Science Ltd. Ail rights reserved.

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页码：8995 / 8998

页数：4

相关论文

共 18 条

[1] PHENOL OXIDATION AND BIOSYNTHESIS .22. ALKALOIDS OF ERYTHRINA-LYSISTEMON, E-ABYSSINICA, E-POEPPIGIANA, E-FUSCA, AND ERYTHRINA-LITHOSPERMA - STRUCTURE OF ERYTHRATIDINE [J].

BARTON, DHR ;

GUNATILA.AA ;

LETCHER, RM ;

LOBO, AMFT ;

WIDDOWSO.DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (08) :874-880

[2] A NOVEL AND PRACTICAL ACCESS TO 13-EPI-17-KETOSTEROIDS [J].

BOIVIN, J ;

SCHIANO, AM ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1992, 33 (51) :7849-7852

[3] A VERSATILE RADICAL-BASED SYNTHESIS OF GAMMA-LACTAMS USING NICKEL POWDER ACETIC-ACID [J].

BOIVIN, J ;

YOUSFI, M ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1994, 35 (31) :5629-5632

[4] A NEW AND PRACTICAL SYNTHESIS OF INDOLONES [J].

BOIVIN, J ;

YOUSFI, M ;

ZARD, SZ .

TETRAHEDRON LETTERS, 1994, 35 (51) :9553-9556

[5] β- and γ-lactams by nickel powder mediated 4-exo or 5-endo radical cyclisations.: A concise construction of the mesembrine skeleton [J].

Cassayre, J ;

Quiclet-Sire, B ;

Saunier, JB ;

Zard, SZ .

TETRAHEDRON, 1998, 54 (07) :1029-1040

[6] TOTAL SYNTHESIS OF +/-3-DEMETHOXYERYTHRATIDINONE - DEMONSTRATION OF A RADICAL CYCLIZATION ROUTE TO A SITE SPECIFIC ENOL DERIVATIVE [J].

DANISHEFSKY, SJ ;

PANEK, JS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :917-918

[7] Manganese(III) reactions in N-heterocycle synthesis:: The preparation of substituted pyrrolidinones [J].

Davies, DT ;

Kapur, N ;

Parsons, AF .

TETRAHEDRON LETTERS, 1998, 39 (24) :4397-4400

[8]

GOODALL K, 1996, TETRAHEDRON, V52, P1069

[9] Regiochemistry in radical cyclisations (4-exo-trig versus 5-endo-trig) of 2-halo-N-(3,4-dihydro-2-naphthyl)acetamides [J].

Ikeda, M ;

Ohtani, S ;

Yamamoto, T ;

Sato, T ;

Ishibashi, H .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (11) :1763-1768

[10] SYNTHESES OF AN ALKALOID, (+/-)-3-DEMETHOXYERYTHRATIDINONE [J].

IRIE, H ;

SHIBATA, K ;

MATSUNO, K ;

ZHANG, Y .

HETEROCYCLES, 1989, 29 (06) :1033-1035