Gold(I)-catalyzed cycloisomerization of 1,7-and 1,8-enynes: Application to the synthesis of a new allocolchicinoid

被引:51
作者
Boyer, Francois-Didier [3 ]
Le Goff, Xavier [2 ]
Hanna, Issam [1 ]
机构
[1] Ecole Polytech, CNRS, UMR 7652, Synth Organ Lab, F-91128 Palaiseau, France
[2] Ecole Polytech, CNRS, UMR 7653, Lab Heteroatomes & Coordinat, F-91128 Palaiseau, France
[3] INRA, Unite Chim Biol, F-78026 Versailles, France
关键词
D O I
10.1021/jo800797c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Gold(I)-catalyzed cycloisomerization of 1,7- and 1,8-enyne propargylic acetates afforded cyclopropyl derivatives containing seven- and eight-membered rings, respectively. This reaction was used for the synthesis of a new allocolchicinoid having a cyclopropane ring fused to the B seven-membered ring at the C6-C7 positions.
引用
收藏
页码:5163 / 5166
页数:4
相关论文
共 39 条
[21]   Allocolchicinoid synthesis via direct arylation [J].
Leblanc, M ;
Fagnou, K .
ORGANIC LETTERS, 2005, 7 (14) :2849-2852
[22]   Mechanistic aspects of transition metal catalysed 1,6-diene and 1,6-enyne cycloisomerisation reactions [J].
Lloyd-Jones, GC .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (02) :215-236
[23]  
Mainetti E, 2002, ANGEW CHEM INT EDIT, V41, P2132, DOI 10.1002/1521-3773(20020617)41:12<2132::AID-ANIE2132>3.0.CO
[24]  
2-S
[25]   Platinum- and gold-catalyzed cycloisomerization reactions of hydroxylated enynes [J].
Mamane, V ;
Gress, T ;
Krause, H ;
Fürstner, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8654-8655
[26]   Recent developments in the metal-catalyzed reactions of metallocarbenoids from propargylic esters [J].
Marco-Contelles, Jose ;
Soriano, Elena .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (05) :1350-1357
[27]   AuI-catalyzed cycloisomerization of 1,5-enynes bearing a propargylic acetate:: formation of unexpected bicyclo[3.1.0]hexene [J].
Marion, N ;
de Frémont, P ;
Lemière, G ;
Stevens, ED ;
Fensterbank, L ;
Malacria, M ;
Nolan, SP .
CHEMICAL COMMUNICATIONS, 2006, (19) :2048-2050
[28]  
MARION N, 2007, CHEM INT ED, V46, P2750
[29]   AuI-catalyzed tandem [3,3] rearrangement-intramolecular hydroarylation:: Mild and efficient formation of substituted indenes [J].
Marion, Nicolas ;
Diez-Gonzalez, Silvia ;
de Fremont, Pierre ;
Noble, April R. ;
Nolan, Steven P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (22) :3647-3650
[30]   Phosphine gold(I) Bis-(trifluoromethanesulfonyl)imidate complexes as new highly efficient and air-stable catalysts for the cycloisomerization of enynes [J].
Mézailles, N ;
Ricard, L ;
Gagosz, F .
ORGANIC LETTERS, 2005, 7 (19) :4133-4136