SYNTHESIS OF (+/-)-PENTALENENE

被引:28
作者
ZHAO, SK [1 ]
MEHTA, G [1 ]
HELQUIST, P [1 ]
机构
[1] UNIV NOTRE DAME,DEPT CHEM & BIOCHEM,NOTRE DAME,IN 46556
关键词
D O I
10.1016/S0040-4039(00)93547-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A short, formal synthesis is reported for pentalenene. The key steps are copper-catalyzed 1,4-addition of isobutylmagnesium bromide to a cyclooctenone derivative, enolate alkylation with the thiocarbene complex [(eta-5-C5H5)(CO)2Fe = CHSPh]+PF6-, and cyclopentane ring formation by means of intramolecular C-H insertion, leading to a late intermediate in a previously reported synthesis of pentalenene.
引用
收藏
页码:5753 / 5756
页数:4
相关论文
共 25 条
[1]   BIOSYNTHESIS OF PENTALENENE AND PENTALENOLACTONE [J].
CANE, DE ;
OLIVER, JS ;
HARRISON, PHM ;
ABELL, C ;
HUBBARD, BR ;
KANE, CT ;
LATTMAN, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4513-4524
[2]   PROTECTION OF HYDROXYL GROUPS AS TERT-BUTYLDIMETHYLSILYL DERIVATIVES [J].
COREY, EJ ;
VENKATESWARLU, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (17) :6190-+
[3]   INTRAMOLECULAR PHOTOCYCLOADDITIONS CYCLOBUTANE FRAGMENTATION - TOTAL SYNTHESIS OF (+/-)-PENTALENENE, (+/-)-PENTALENIC ACID, AND (+/-)-DEOXYPENTALENIC ACID [J].
CRIMMINS, MT ;
DELOACH, JA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :800-806
[4]  
GOPALAKRISHNAN G, 1985, INDIAN J CHEM B, V24, P765
[5]   ME3SICL/HMPA ACCELERATED CONJUGATE ADDITION OF CATALYTIC COPPER REAGENT - STEREOSELECTIVE SYNTHESIS OF ENOL SILYL ETHER OF ALDEHYDE [J].
HORIGUCHI, Y ;
MATSUZAWA, S ;
NAKAMURA, E ;
KUWAJIMA, I .
TETRAHEDRON LETTERS, 1986, 27 (34) :4025-4028
[6]   DOES ME3SICL ACTIVATE CONJUGATE ADDITION OF COPPER REAGENTS AS A LEWIS ACID [J].
HORIGUCHI, Y ;
KOMATSU, M ;
KUWAJIMA, I .
TETRAHEDRON LETTERS, 1989, 30 (50) :7087-7090
[7]  
HUA D H, 1986, Journal of the American Chemical Society, V108, P3835, DOI 10.1021/ja00273a052
[8]   SYSTEM ORIENTED DESIGN OF TRIQUINANES - STEREOCONTROLLED SYNTHESIS OF PENTALENIC ACID AND PENTALENENE [J].
HUDLICKY, T ;
SINAIZINGDE, G ;
NATCHUS, MG ;
RANU, BC ;
PAPADOPOLOUS, P .
TETRAHEDRON, 1987, 43 (23) :5685-5721
[9]   TOTAL SYNTHESIS OF (+/-)-PENTALENENE, (+/-)-PENTALENIC ACID, AND (+/-)-DEOXYPENTALENIC ACID THROUGH AN INTRAMOLECULAR DOUBLE MICHAEL REACTION [J].
IHARA, M ;
KATOGI, M ;
FUKUMOTO, K ;
KAMETANI, T .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (11) :2963-2970
[10]  
IMANISHI T, 1990, CHEM PHARM BULL, V38, P1124