REACTIONS WITH ALKENES OF ETA-2-7-OXOTETRACARBONYLMANGANESE COMPLEXES DERIVED FROM DITERPENOIDS

被引:33
作者
CAMBIE, RC [1 ]
METZLER, MR [1 ]
RUTLEDGE, PS [1 ]
WOODGATE, PD [1 ]
机构
[1] UNIV AUCKLAND,DEPT CHEM,AUCKLAND,NEW ZEALAND
关键词
D O I
10.1016/0022-328X(92)83318-C
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A number of activated 7-oxotetracarbonylmanganese(I) complexes derived from podocarpic acid (1) and from dehydroabietic acid have been coupled with alkenes to give C(14) functionalised derivatives in high yields. Some coupling reactions resulted in cyclization to C(7), forming 4H-acephenanthrylene derivatives in moderate yields. Several modes of activating these manganese complexes towards coupling reactions were investigated; these included oxidative decarbonylation at room temperature, thermal promotion, and palladium-mediation.
引用
收藏
页码:59 / 86
页数:28
相关论文
共 28 条
[1]   REGIOCHEMISTRY OF PALLADIUM-CATALYZED ARYLATION REACTIONS OF ENOL ETHERS - ELECTRONIC CONTROL OF SELECTION FOR ALPHA-ARYLATION OR BETA-ARYLATION [J].
ANDERSSON, CM ;
HALLBERG, A ;
DAVES, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3529-3536
[2]   3 ISOMERIC 1,3-DIMETHYL-5-(DIHYDROPYRAN-2'-YL)-2,4-PYRIMIDINEDIONES - PALLADIUM-CATALYZED SYNTHESIS AND SPECTROMETRIC PROPERTIES [J].
ARAI, I ;
DAVES, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4110-4112
[3]   REGIOSPECIFIC REACTION OF ENOL ETHERS WITH AN ORGANOPALLADIUM SALT - STEREOCHEMICAL AND CONFORMATIONAL EFFECTS ON PRODUCT FORMATION [J].
ARAI, I ;
DAVES, GD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (01) :287-288
[4]   PALLADIUM-CATALYZED PHENYLATION OF ENOL ETHERS AND ACETATES [J].
ARAI, I ;
DAVES, GD .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (01) :21-23
[5]   CYCLOMETALATION REACTIONS [J].
BRUCE, MI .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (02) :73-86
[6]   ORGANOMANGANESE COMPLEXES OF PODOCARPIC ACID-DERIVATIVES [J].
CAMBIE, RC ;
METZLER, MR ;
RICKARD, CEF ;
RUTLEDGE, PS ;
WOODGATE, PD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1992, 425 (1-2) :59-87
[7]   SYNTHESIS AND REACTIONS OF ETA-2-(2-FORMYLPHENYL)TETRACARBONYLMANGANESE(I) COMPLEXES - CYCLOPENTAANNULATION OF A DITERPENOID [J].
CAMBIE, RC ;
METZLER, MR ;
RUTLEDGE, PS ;
WOODGATE, PD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 398 (03) :C22-C24
[8]   CYCLOMANGANATION OF DITERPENOIDS - FUNCTIONALIZATION OF C-14 [J].
CAMBIE, RC ;
METZLER, MR ;
RUTLEDGE, PS ;
WOODGATE, PD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 381 (01) :C26-C30
[9]   CHEMISTRY OF THE PODOCARPACEAE .71. PREPARATION, STRUCTURE, AND REACTIONS OF SOME (ARENE)TRICARBONYLCHROMIUM(0) COMPLEXES - CRYSTAL-STRUCTURE OF ALPHA-TRICARBONYL[(8,9,11,12,13,14-ETA)-METHYL PODOCARPA-8,11,13-TRIEN-19-OATE]CHROMIUM(0) [J].
CAMBIE, RC ;
CLARK, GR ;
GALLAGHER, SR ;
RUTLEDGE, PS ;
STONE, MJ ;
WOODGATE, PD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1988, 342 (03) :315-337
[10]   CHEMISTRY OF THE PODOCARPACEAE .70. SYNTHESIS AND CYCLOPENTAANNULATION OF A DITERPENOID CHROMIUM CARBENE COMPLEX [J].
CAMBIE, RC ;
RUTLEDGE, PS ;
TERCEL, M ;
WOODGATE, PD .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 315 (02) :171-185