Pt-catalyzed tandem epoxide fragmentation/pentannulation of propargylic esters

被引:87
作者
Pujanauski, Brian G. [1 ]
Prasad, B. A. Bhanu [1 ]
Sarpong, Richmond [1 ]
机构
[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ja061549m
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A Pt-catalyzed pentannulation of propargylic esters containing an epoxide moiety has been developed. The present transformation achieves the formation of cyclopentenone products as single diastereomers in good yields. The observed products likely form from pyran intermediates that undergo an oxa-6π electrocyclic ring opening to a functionalized dienone, followed by ring closure with an accompanying acyl shift. Copyright © 2006 American Chemical Society.
引用
收藏
页码:6786 / 6787
页数:2
相关论文
共 20 条
[1]   Tandem PtCl2 catalyzed-thermal [3,3] rearrangements of enyne acetates [J].
Cariou, K ;
Mainetti, E ;
Fensterbank, L ;
Malacria, M .
TETRAHEDRON, 2004, 60 (43) :9745-9755
[2]   The Nazarov cyclization in organic synthesis. Recent advances [J].
Frontier, AJ ;
Collison, C .
TETRAHEDRON, 2005, 61 (32) :7577-7606
[3]  
Geis O, 1998, ANGEW CHEM INT EDIT, V37, P911, DOI 10.1002/(SICI)1521-3773(19980420)37:7<911::AID-ANIE911>3.0.CO
[4]  
2-O
[5]   PtCl2-catalyzed cycloisomerizations of 5-En-1-yn-3-ol systems [J].
Harrak, Y ;
Blaszykowski, C ;
Bernard, M ;
Cariou, K ;
Mainetti, E ;
Mouriès, V ;
Dhimane, AL ;
Fensterbank, L ;
Malacria, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (28) :8656-8657
[6]   THERMAL CYCLIZATION OF ALPHA-ALKYNONES TO 2-CYCLOPENTENONES [J].
KARPF, M ;
DREIDING, AS .
HELVETICA CHIMICA ACTA, 1979, 62 (03) :852-865
[7]  
Mainetti E, 2002, ANGEW CHEM INT EDIT, V41, P2132, DOI 10.1002/1521-3773(20020617)41:12<2132::AID-ANIE2132>3.0.CO
[8]  
2-S
[9]   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
[10]   Catalytic isomerization of 1-alkynyl-2,3-epoxy alcohols to substituted furans: Succinct routes to furanoid fatty acids and difurylmethanes [J].
Marson, CM ;
Harper, S .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9223-9231