NEW EFFICIENT PROTOCOL FOR ARYNE GENERATION - SELECTIVE SYNTHESIS OF DIFFERENTIALLY PROTECTED 1,4,5-NAPHTHALENETRIOLS

被引:138
作者
MATSUMOTO, T [1 ]
HOSOYA, T [1 ]
KATSUKI, M [1 ]
SUZUKI, K [1 ]
机构
[1] KEIO UNIV,DEPT CHEM,KOHOKU KU,YOKOHAMA,KANAGAWA 223,JAPAN
关键词
D O I
10.1016/S0040-4039(00)93589-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Arynes are generated cleanly and rapidly by halogen-lithium exchange of ortho-haloaryl triflates with n-BuLi at -78-degrees-C. [2+4]-Cycloaddition of alpha-alkoxyaryne with 2-methoxyfuran proceeded regioselectively (head-to-head) to afford 1,4,5-naphthalenetriols.
引用
收藏
页码:6735 / 6736
页数:2
相关论文
共 12 条
[1]   A CONCISE TOTAL SYNTHESIS OF THE AGLYCONE OF THE GILVOCARCINS [J].
DESHPANDE, PP ;
MARTIN, OR .
TETRAHEDRON LETTERS, 1990, 31 (44) :6313-6316
[2]   TWIN BENZOANNULATION OF NAPHTHALENE VIA 1,3-NAPHTHODIYNE, 1,6-NAPHTHODIYNE, AND 2,6-NAPHTHODIYNE SYNTHETIC EQUIVALENTS - NEW SYNTHESES OF TRIPHENYLENE, BENZ[A]ANTHRACENE, AND NAPHTHACENE [J].
GRIBBLE, GW ;
PERNI, RB ;
ONAN, KD .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (16) :2934-2939
[3]  
HAYES NF, 1957, J CHEM SOC, P904
[4]   FLUORIDE-INDUCED 1,2-ELIMINATION OF ORTHO-TRIMETHYLSILYLPHENYL TRIFLATE TO BENZYNE UNDER MILD CONDITIONS [J].
HIMESHIMA, Y ;
SONODA, T ;
KOBAYASHI, H .
CHEMISTRY LETTERS, 1983, (08) :1211-1214
[5]  
Hoffmann R. W., 1967, DEHYDROBENZENE CYCLO
[6]  
LAATSCH H, 1980, LIEBIGS ANN CHEM, P1321
[7]   A STRATEGY FOR THE CONVERGENT SYNTHESIS OF GILVOCARCINS VIA CHROMIUM CARBENE BENZANNULATION - 1-O-METHYLDEFUCOGILVOCARCIN-V IN 7 STEPS [J].
PARKER, KA ;
COBURN, CA .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (04) :1666-1668
[8]   APPROACHES TO ANTHRACYCLINES - EFFICIENT SYNTHESES OF SUBSTITUTED NAPHTHYLACETONITRILES [J].
PARKER, KA ;
IQBAL, T .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (06) :1149-1151
[9]   HETARYNES [J].
REINECKE, MG .
TETRAHEDRON, 1982, 38 (04) :427-498
[10]   SILICON IN BENZAMIDE DIRECTED ORTHO METALATION - FORMATION AND REACTIONS OF BENZAMIDE BENZYNES [J].
SHANKARAN, K ;
SNIECKUS, V .
TETRAHEDRON LETTERS, 1984, 25 (27) :2827-2830