Aromatic enynes as substrates for the intramolecular Pauson-Khand reaction

被引:12
作者
Blanco-Urgoiti, J [1 ]
Casarrubios, L [1 ]
Pérez-Castells, J [1 ]
机构
[1] Univ San Pablo, CEU, Fac CC Expt & Tecn, Dept Quim Organ & Farmaceut, Madrid 28668, Spain
关键词
D O I
10.1016/S0040-4039(99)00268-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pauson-Khand reactions are carried out with different substituted aromatic enynes yielding tricyclic cyclopentenones related to natural products. Reaction is promoted by dissolved Me3NO. Isomerization of the double bond of the cyclopentenone is observed except for compound 2e, with a non terminal triple bond. (C) 1999 Elsevier Science Ltd. All rights reserved.
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收藏
页码:2817 / 2820
页数:4
相关论文
共 24 条
[1]   HEXACARBONYL DICOBALT COMPLEXED N-PROP-2-YNYL-2-AZETIDINONES - A NEW ENTRY TO N-UNSUBSTITUTED-BETA-LACTAMS THROUGH A NICHOLAS-TYPE REACTION [J].
ALCAIDE, B ;
PEREZCASTELLS, J ;
SANCHEZVIGO, B ;
SIERRA, MA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (05) :587-588
[2]   THE SYNTHESIS OF NITROGEN-HETEROCYCLES VIA THE INTRAMOLECULAR KHAND REACTION - FORMATION OF TETRA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXA-HYDROCYCLOPENTA[C]PYRROL-5(1H)-ONES AND HEXAHYDRO-6H-2-PYRINDIN-6-ONES [J].
BROWN, SW ;
PAUSON, PL .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (04) :1205-1209
[3]   Ready access to bicyclo[5.3.0]decan-1-ones and to bicyclo[6.3.0]undecan-1-ones by intramolecular Pauson-Khand reactions using a temporary sulfur bridge [J].
Castro, J ;
Moyano, A ;
Pericas, MA ;
Riera, A .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (10) :3346-3351
[4]   PROMOTERS FOR THE (ALKYNE)HEXACARBONYLDICOBALT-BASED CYCLOPENTENONE SYNTHESIS [J].
CHUNG, YK ;
LEE, BY ;
JEONG, N ;
HUDECEK, M ;
PAUSON, PL .
ORGANOMETALLICS, 1993, 12 (01) :220-223
[5]   STEREOSELECTIVITY OF INTRAMOLECULAR DICOBALT OCTACARBONYL ALKENE ALKYNE CYCLIZATIONS - SHORT SYNTHESIS OF DL-CORIOLIN [J].
EXON, C ;
MAGNUS, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (08) :2477-2478
[6]  
Geis O, 1998, ANGEW CHEM INT EDIT, V37, P911, DOI 10.1002/(SICI)1521-3773(19980420)37:7<911::AID-ANIE911>3.0.CO
[7]  
2-O
[8]  
GORDON AR, 1996, SYNLETT, P1083
[9]  
HUA D H, 1986, Journal of the American Chemical Society, V108, P3835, DOI 10.1021/ja00273a052
[10]  
INGATE ST, 1998, ORG P PREP INT, P123