Novel Pd(0)-catalyzed cyclization-carbonylation of 2-methyl-1-vinyl-5,6-heptadienyl acetate: The synthesis of (+/-)-isoiridomyrmecin

被引:13
作者
Doi, T
Yanagisawa, A
Yamamoto, K
Takahashi, T
机构
[1] SCI UNIV TOKYO, FAC MAT SCI & ENGN, YAMAGUCHI 756, JAPAN
[2] TOKYO INST TECHNOL, DEPT CHEM ENGN, MEGURO KU, TOKYO 152, JAPAN
关键词
D O I
10.1246/cl.1996.1085
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The Pd(0)-catalyzed cyclization-carbonylation of 2-methyl-1-vinyl-5,6-heptadienyl acetate regio- and stereoselectively gave an alpha-cyclopentylacrylic acid derivative which was applied to the synthesis of (+/-)-isoiridomyrmecin.
引用
收藏
页码:1085 / 1086
页数:2
相关论文
共 35 条
[21]   PALLADIUM(II)-MEDIATED ROUTES TO FUNCTIONALIZED HETEROCYCLES [J].
LATHBURY, D ;
VERNON, P ;
GALLAGHER, T .
TETRAHEDRON LETTERS, 1986, 27 (49) :6009-6012
[22]   FACILE FORMATION OF 7-MEMBERED AND 8-MEMBERED CYCLOALKENES VIA CATALYTIC AND CYCLIC CARBOPALLADATION OF ALLENES [J].
MA, SM ;
NEGISHI, E .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) :4730-4732
[23]   PALLADIUM-CATALYZED CYCLIZATION OF OMEGA-HALOALLENES - A NEW GENERAL-ROUTE TO COMMON, MEDIUM, AND LARGE RING COMPOUNDS VIA CYCLIC CARBOPALLADATION [J].
MA, SM ;
NEGISHI, EI .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (23) :6345-6357
[24]  
Mikami K, 1989, SYNLETT, P45
[25]   ENANTIOSELECTIVE SYNTHESES OF (+)-ALPHA-SKYTANTHINE, (+)-DELTA-SKYTANTHINE AND (+)-IRIDOMYRMECIN BY AN INTRAMOLECULAR MAGNESIUM-ENE REACTION [J].
OPPOLZER, W ;
JACOBSEN, EJ .
TETRAHEDRON LETTERS, 1986, 27 (10) :1141-1144
[26]   MONOTERPENES OF TEUCRIUM-MARUM [J].
PAGNONI, UM ;
PINETTI, A ;
TRAVE, R ;
GARANTI, L .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1976, 29 (06) :1375-1381
[27]   PALLADIUM-CATALYZED CARBOALKOXYLATION OF ARYL, BENZYL, AND VINYLIC HALIDES [J].
SCHOENBE.A ;
BARTOLET.I ;
HECK, RF .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23) :3318-3326
[29]   PALLADIUM-CATALYZED SYNTHESIS OF 2,3-DISUBSTITUTED ALLYLAMINES BY REGIOSELECTIVE AMINOPHENYLATION OR AMINOALKENYLATION OF 1,2-DIENES [J].
SHIMIZU, I ;
TSUJI, J .
CHEMISTRY LETTERS, 1984, (02) :233-236
[30]  
Stevens R. R., 1970, J ORGANOMET CHEM, V21, P495