Synthesis of polycyclic compounds utilizing the nickel-catalysed alkynylstannylation of 1,2-dienes

被引:26
作者
Shirakawa, E [1 ]
Nakao, Y
Tsuchimoto, T
Hiyama, T
机构
[1] Japan Adv Inst Sci & Technol, Grad Sch Mat Sci, Tatsunokuchi, Ishikawa 9231292, Japan
[2] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
关键词
D O I
10.1039/b206240b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Polycyclic compounds having linearly-fused six-membered rings can be readily prepared by various modes of cyclization from dienediynes, which were synthesized through the nickel-catalysed alkynylstannylation of 1,2-dienes followed by the palladium-catalysed oxidative homocoupling of the resulting alkenylstannanes.
引用
收藏
页码:1962 / 1963
页数:2
相关论文
共 19 条
[1]   CYCLIC DIENES .27. 1,2,4,5-TETRAMETHYLENECYCLOHEXANE [J].
BAILEY, WJ ;
ECONOMY, J ;
FETTER, EJ .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (10) :3479-&
[2]  
Fugami K, 2002, TOP CURR CHEM, V219, P87
[3]   PREPARATION AND SELECTED REACTIONS OF 2,3-BIS(BROMOMETHYL)-1,3-BUTADIENE [J].
GAONI, Y ;
SADEH, S .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (05) :870-881
[4]   Cuprous chloride accelerated Stille reactions. A general and effective coupling system for sterically congested substrates and for enantioselective synthesis [J].
Han, XJ ;
Stoltz, BM ;
Corey, EJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) :7600-7605
[5]  
HOPF H, 2000, CLASSICS HYDROCARBON, P423
[6]   TOTAL SYNTHESIS OF ANTHRACYCLINONE [J].
KROHN, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (09) :790-807
[7]   A NONAROMATIC ROUTE TO A PARACYCLOPHANE - A STUDY OF 1,2,4,5-TETRAMETHYLENECYCLOHEXANE TO TETRAMETHYL[2.2]PARACYCLOPHANE CONVERSION [J].
LONGONE, DT ;
BOETTCHER, FP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (21) :3436-&
[8]   Mild and efficient formation of symmetric biaryls via Pd(II) catalysts and Cu(II) oxidants [J].
Parrish, JP ;
Flanders, VL ;
Floyd, RJ ;
Jung, KW .
TETRAHEDRON LETTERS, 2001, 42 (44) :7729-7731
[9]   ASYMMETRIC-SYNTHESIS OF ISOINDOLINE, AND ISOQUINOLINE DERIVATIVES USING NICKEL(0)-CATALYZED [2+2+2]-COCYCLIZATION [J].
SATO, Y ;
NISHIMATA, T ;
MORI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (21) :6133-6135
[10]   Palladium-catalyzed dimerization-carbostannylation of alkynes: Synthesis of highly conjugated alkenylstannanes [J].
Shirakawa, E ;
Yoshida, H ;
Nakao, Y ;
Hiyama, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4290-4291