ARYL-SUBSTITUTED CYCLOHEXADIENYL COMPLEXES - NOVEL INTERMEDIATES FOR AN ORGANOMETALLIC APPROACH TO SCELETIUM AND AMARYLLIDACEAE ALKALOID SYNTHESIS

被引:35
作者
OWEN, DA [1 ]
STEPHENSON, GR [1 ]
FINCH, H [1 ]
SWANSON, S [1 ]
机构
[1] GLAXO GRP RES LTD,WARE SG12 0DJ,HERTS,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)97407-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of 1-phenyl substituted tricarbonyl(π5-cyclohexadienyl)iron(l+) complexes is described. Although 1-phenyl substituents were found to direct nucleophiles to the far end of the β-system, this effect could be overcome by a methoxyl substituent at C-4, permitting a regio- and stereocontrolled alkylation step that forms a quaternary centre required in Sceletium and Amaryllidaceae alkaloid synthesis. © 1990.
引用
收藏
页码:3401 / 3404
页数:4
相关论文
共 11 条
[1]  
Birch A. J., 1977, ORG SYNTH, V57, P107
[2]  
BIRCH AJ, 1975, TETRAHEDRON LETT, P119
[3]   CHEMISTRY OF CO-ORDINATED LIGANDS .2. IRON TRICARBONYL COMPLEXES OF SOME CYCLOHEXADIENES [J].
BIRCH, AJ ;
CROSS, PE ;
LEWIS, J ;
WHITE, DA ;
WILD, SB .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1968, (02) :332-&
[4]   TRICARBONYLIRON METHOXYCYCLOHEXADIENE AND DIENYL COMPLEXES - PREPARATION, PROPERTIES AND APPLICATIONS [J].
BIRCH, AJ ;
KELLY, LF .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :267-280
[5]   TRANSITION-METAL MEDIATED ASYMMETRIC-SYNTHESIS .10. HOMOCHIRAL PI-COMPLEXES WITH PLANAR CHIRALITY - SYNTHETIC EQUIVALENTS OF CHIRAL CYCLOHEXADIENE DICATIONS [J].
HOWARD, PW ;
STEPHENSON, GR ;
TAYLOR, SC .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 370 (1-3) :97-109
[6]   TRANSITION-METAL DIENE COMPLEXES IN ORGANIC-SYNTHESIS .3. IRON-MEDIATED DIASTEREOSELECTIVE SPIROANNELATION TO THE SPIRO[1,2,3,4-TETRAHYDROQUINOLINE-4,1'-CYCLOHEXANE] SYSTEM AND A NOVEL REARRANGEMENT TO 2,3-DIHYDROINDOLE DERIVATIVES [J].
KNOLKER, HJ ;
BOESE, R ;
HARTMANN, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (12) :1678-1679
[7]   1ST ALKYLATION OF A 1-METHOXY-SUBSTITUTED TRICARBONYL(ETA-5-CYCLOHEXADIENYL)IRON(1 +) COMPLEX [J].
PALOTAI, IM ;
STEPHENSON, GR ;
ROSS, WJ ;
TUPPER, DE .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1989, 364 (1-2) :C11-C14
[8]   A CONVERGENT APPROACH TO THE SYNTHESIS OF (+/-)-O-METHYLJOUBERTIAMINE USING ORGANOIRON COMPLEXES [J].
PEARSON, AJ ;
RICHARDS, IC ;
GARDNER, DV .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (14) :807-809
[9]   A NOVEL SYNTHESIS OF 4-ALKYL-4-(4-METHOXYPHENYL)CYCLOHEX-2-EN-1-ONES AND THE SCELETIUM ALKALOID, O-METHYLJOUBERTIAMINE [J].
SCHULTE, LD ;
RIEKE, RD .
TETRAHEDRON LETTERS, 1988, 29 (43) :5483-5486
[10]   PI-COMPLEXES WITH PLANAR CHIRALITY - CONTROL CENTERS FOR STEREOSELECTIVE SYNTHESIS [J].
STEPHENSON, GR ;
ALEXANDER, RP ;
MORLEY, C ;
HOWARD, PW .
PHILOSOPHICAL TRANSACTIONS OF THE ROYAL SOCIETY A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES, 1988, 326 (1592) :545-556