VERSATILE SYNTHESIS OF TROPONES BY REACTION OF RHODIUM(II)-STABILIZED VINYLCARBENOIDS WITH 1-METHOXY-1-[(TRIMETHYLSILYL)OXY]BUTA-1,3-DIENE

被引：54

作者：

DAVIES, HML

CLARK, TJ

KIMMER, GF

机构：

[1] Department of Chemistry, Wake Forest University, Winston-Salem, North Carolina 27109

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 22期

关键词：

D O I：

10.1021/jo00022a041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(II)-catalyzed decomposition of vinyldiazomethanes in the presence of 1-methoxy-1-[(trimethylsilyl)oxy]buta-1,3-diene leads to [3 + 4] annulation products by a tandem cyclopropanation/Cope rearrangement sequence. The resulting cycloheptadienes are readily converted to cycloheptatrienones either by hydrolysis with mild acid followed by oxidation with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or by treatment with dichloroethoxyoxovanadium. The efficiency of the general strategy was demonstrated through a short synthesis of nezukone.

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页码：6440 / 6447

页数：8

相关论文

共 68 条

[1] A DIHYDRO-ALPHA-FUROIC ESTER SYNTHESIS BY THE CATALYZED-REACTIONS OF ETHYL DIAZOPYRUVATE WITH ENOL ETHERS [J].

ALONSO, ME ;

JANO, P ;

HERNANDEZ, MI ;

GREENBERG, RS ;

WENKERT, E .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (18) :3047-3050

[2] STUDIES ON THE ORIGIN OF DIHYDROFURANS FROM ALPHA-DIAZOCARBONYL COMPOUNDS - CONCERTED 1,3-DIPOLAR CYCLOADDITION VS NONSYNCHRONOUS COUPLING IN THE COPPER CHELATE CATALYZED-REACTIONS OF ALPHA-DIAZODICARBONYL COMPOUNDS WITH ELECTRON-RICH OLEFINS [J].

ALONSO, ME ;

MORALES, A ;

CHITTY, AW .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (19) :3747-3754

[3] OXIDATION OF VICINAL DIOLS TO ALPHA-DICARBONYL COMPOUNDS BY TRIFLUOROACETIC-ANHYDRIDE ACTIVATED DIMETHYLSULFOXIDE [J].

AMON, CM ;

BANWELL, MG ;

GRAVATT, GL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4851-4855

[4]

ANDERSON AB, 1933, J AM CHEM SOC, V55, P3813

[5]

ASAO T, 1985, METHODEN ORGANISCHEN, V5, P710

[6] A NEW AND SIMPLE SYNTHESIS OF TROPONES [J].

BANWELL, MG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (15) :847-848

[7] A VERSATILE NEW STRATEGY FOR THE SYNTHESIS OF TROPOLONES [J].

BANWELL, MG ;

ONRUST, R .

TETRAHEDRON LETTERS, 1985, 26 (37) :4543-4546

[8] A SYNTHESIS OF STIPITATIC ACID [J].

BARTELSKEITH, JR ;

JOHNSON, AW ;

TAYLOR, WI .

JOURNAL OF THE CHEMICAL SOCIETY, 1951, (SEP) :2352-2356

[9] DIELS-ALDER CYCLOADDITION REACTIONS OF CYCLOPROPENONE KETALS - DUAL PARTICIPATION IN INVERSE ELECTRON DEMAND (LUMODIENE CONTROLLED) AND NORMAL ]HOMODIENE CONTROLLED) DIELS-ADLER REACTIONS, APPROACHES TO THE PREPARATION OF TROPONES [J].

BOGER, DL ;

BROTHERTON, CE .

TETRAHEDRON, 1986, 42 (11) :2777-2785

[10] THERMAL-REACTIONS OF CYCLOPROPENONE KETALS - APPLICATION OF THE CYCLOADDITION REACTIONS OF DELOCALIZED SINGLET VINYLCARBENES - 3-CARBON 1,1-DIPOLES 1,3-DIPOLES - AN ALTERNATIVE SYNTHESIS OF DEACETAMIDOCOLCHICEINE - FORMAL TOTAL SYNTHESIS OF COLCHICINE [J].

BOGER, DL ;

BROTHERTON, CE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (21) :6713-6719

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