A highly regio- and stereoselective carbocupration of fluoroalkylated internal alkynes: A short total synthesis of the antiestrogenic drug panomifene

被引:72
作者
Konno, T [1 ]
Daitoh, T [1 ]
Noiri, A [1 ]
Chae, J [1 ]
Ishihara, T [1 ]
Yamanaka, H [1 ]
机构
[1] Kyoto Inst Technol, Dept Chem & Mat Technol, Sakyo Ku, Kyoto 6068585, Japan
关键词
D O I
10.1021/ol036440n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A highly regio- and stereoselective carbometalation reaction of fluoroalkylated internal alkynes with organocopper reagents is described. This reaction is utilized successfully in the short, stereoselective total synthesis of the antiestrogenic drug panomifene.
引用
收藏
页码:933 / 936
页数:4
相关论文
共 35 条
[1]  
ABRAHAM G, 1979, Patent No. 17853
[2]  
ALHASSAN MI, 1987, SYNTHESIS-STUTTGART, P816
[3]  
[Anonymous], 1990, DRUGS FUT, V15, P532
[4]   Hydrofluorocarbon 245fa: a versatile new synthon in alkyne chemistry [J].
Brisdon, AK ;
Crossley, IR .
CHEMICAL COMMUNICATIONS, 2002, (20) :2420-2421
[5]   ARYL TRIFLUOROMETHYL ACETYLENES [J].
BUNCH, JE ;
BUMGARDNER, CL .
JOURNAL OF FLUORINE CHEMISTRY, 1987, 36 (03) :313-317
[6]   A FACILE AND PRACTICAL SYNTHESIS OF 1-ARYL-3,3,3-TRIFLUOROPROPYNES [J].
HIYAMA, T ;
SATO, K ;
FUJITA, M .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (04) :1352-1354
[7]   SYNTHESIS OF TRIFLUOROMETHYL-SUBSTITUTED CONJUGATED ENYNES INCLUDING A FLUORINATED SICCAYNE [J].
HU, CM ;
HONG, F ;
XU, YY .
JOURNAL OF FLUORINE CHEMISTRY, 1993, 64 (1-2) :1-4
[8]   SYNTHESIS OF ARYLTRIFLUOROMETHYLACETYLENES [J].
KOBAYASHI, Y ;
YAMASHITA, T ;
TAKAHASHI, K ;
KURODA, H ;
KUMADAKI, I .
TETRAHEDRON LETTERS, 1982, 23 (03) :343-344
[9]   Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives [J].
Konno, T ;
Chae, J ;
Kanda, M ;
Nagai, G ;
Tamura, K ;
Ishihara, T ;
Yamanaka, H .
TETRAHEDRON, 2003, 59 (38) :7571-7580
[10]  
KONNO T, UNPUB CHEM COMMUN