PtCl2-catalyzed cycloisomerizations of 5-En-1-yn-3-ol systems

被引:208
作者
Harrak, Y [1 ]
Blaszykowski, C [1 ]
Bernard, M [1 ]
Cariou, K [1 ]
Mainetti, E [1 ]
Mouriès, V [1 ]
Dhimane, AL [1 ]
Fensterbank, L [1 ]
Malacria, M [1 ]
机构
[1] Univ Paris 06, CNRS, UMR 7611, Chim Organ Lab, F-75252 Paris 05, France
关键词
D O I
10.1021/ja0474695
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
5-En-1-yn-3-ol substrates bearing a free hydroxyl group or an acyl group are highly versatile partners for PtCl2-catalyzed cycloisomerizations. Electrophilic activation of the alkyne moiety triggers at wish a hydride or an O-acyl migration yielding at the end to regioisomeric keto derivatives. The efficient preparation of Sabina ketone, an important monoterpene precursor, has been worked out. Copyright © 2004 American Chemical Society.
引用
收藏
页码:8656 / 8657
页数:2
相关论文
共 22 条
[1]   The behavior of 1,n-enynes in the presence of transition metals [J].
Aubert, C ;
Buisine, O ;
Malacria, M .
CHEMICAL REVIEWS, 2002, 102 (03) :813-834
[2]   Enantioselective synthesis of sabina ketone [J].
Barberis, M ;
Pérez-Prieto, J .
TETRAHEDRON LETTERS, 2003, 44 (35) :6683-6685
[3]   PtCl2-catalyzed cycloisomerizations of allenynes [J].
Cadran, N ;
Cariou, K ;
Hervé, G ;
Aubert, C ;
Fensterbank, L ;
Malacria, M ;
Marco-Contelles, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) :3408-3409
[4]  
CHAMAULT L, 2004, CHEM COMMUN, P850
[5]   Construction of novel polycyclic ring systems by transition-metal-catalyzed cycloisomerization of ene-ene-ynes. Interception of a carbenoid intermediate in skeletal reorganization of enynes [J].
Chatani, N ;
Kataoka, K ;
Murai, S ;
Furukawa, N ;
Seki, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (35) :9104-9105
[6]   Platinum-catalyzed cycloisomerization reactions of enynes [J].
Fürstner, A ;
Stelzer, F ;
Szillat, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (48) :11863-11869
[7]   Platinum- and acid-catalyzed enyne metathesis reactions:: Mechanistic studies and applications to the syntheses of streptorubin B and metacycloprodigiosin [J].
Fürstner, A ;
Szillat, H ;
Gabor, B ;
Mynott, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) :8305-8314
[8]   A short and efficient synthesis of (±)-trans-sabinene hydrate [J].
Galopin, CC .
TETRAHEDRON LETTERS, 2001, 42 (33) :5589-5591
[9]   Photoinduced electron transfer reactions of alpha-cyclopropyl- and alpha-epoxy ketones. Tandem fragmentation-cyclization to bi-, tri-, and spirocyclic ketones [J].
Kirschberg, T ;
Mattay, J .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (25) :8885-8896
[10]   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