HIGHLY SELECTIVE SYNTHESIS OF VITAMIN-A AND ITS DERIVATIVES - CRITICAL COMPARISON OF SOME KNOWN PALLADIUM-CATALYZED ALKENYL-ALKENYL COUPLING REACTIONS

被引:65
作者
NEGISHI, E
OWCZARCZYK, Z
机构
[1] Department of Chemistry, Purdue University, West Lafayette
关键词
D O I
10.1016/S0040-4039(00)93574-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Vitamin A has been synthesized cleanly and selectively with essentially complete control of stereo- and regiochemistry in four linear and six overall steps from beta-ionone and (E)-3-methyl-2-penten-4-yn-1-ol via Pd-catalyzed cross coupling of an alkenylzinc with an alkenyl iodide; the use of other metals, such as Al, Zr, Mg, B, Cu, and Sn, being inferior to that of Zn.
引用
收藏
页码:6683 / 6686
页数:4
相关论文
共 24 条
  • [1] TOTAL SYNTHESIS OF A FULLY PROTECTED PALYTOXIN CARBOXYLIC-ACID
    ARMSTRONG, RW
    BEAU, JM
    CHEON, SH
    CHRIST, WJ
    FUJIOKA, H
    HAM, WH
    HAWKINS, LD
    JIN, H
    KANG, SH
    KISHI, Y
    MARTINELLI, MJ
    MCWHORTER, WW
    MIZUNO, M
    NAKATA, M
    STUTZ, AE
    TALAMAS, FX
    TANIGUCHI, M
    TINO, JA
    UEDA, K
    UENISHI, J
    WHITE, JB
    YONAGA, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) : 7525 - 7530
  • [2] NOVEL STEREOSPECIFIC ALKENYL-ALKENYL CROSS-COUPLING BY A PALLADIUM-CATALYZED OR NICKEL-CATALYZED REACTION OF ALKENYLALANES WITH ALKENYL HALIDES
    BABA, S
    NEGISHI, E
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (21) : 6729 - 6731
  • [3] DANG HP, 1978, TETRAHEDRON LETT, P191
  • [4] PALLADIUM CATALYSIS IN CEPHALOSPORIN CHEMISTRY - A VERSATILE NEW APPROACH TO 3-SUBSTITUTED CEPHEMS
    FARINA, V
    BAKER, SR
    SAPINO, C
    [J]. TETRAHEDRON LETTERS, 1988, 29 (47) : 6043 - 6046
  • [5] Greene T.W., 1981, PROTECTIVE GROUPS OR
  • [6] ORGANOCOPPER VINYLICS .74. ARYLATION OF VINYLIC CUPRATES
    JABRI, N
    ALEXAKIS, A
    NORMANT, JF
    [J]. TETRAHEDRON LETTERS, 1981, 22 (39) : 3851 - 3852
  • [7] VINYL-COPPER DERIVATIVES .15. AN EFFICIENT SYNTHESIS OF POLYSUBSTITUTED CONJUGATED DIENES
    JABRI, N
    ALEXAKIS, A
    NORMANT, JF
    [J]. TETRAHEDRON LETTERS, 1982, 23 (15) : 1589 - 1592
  • [8] VINYL-COPPER DERIVATIVES .13. SYNTHESIS OF CONJUGATED DIENES OF VERY HIGH STEREOISOMERIC PURITY
    JABRI, N
    ALEXAKIS, A
    NORMANT, JF
    [J]. TETRAHEDRON LETTERS, 1981, 22 (10) : 959 - 962
  • [9] KING O, 1979, THESIS SYRACUSE U, P82
  • [10] PHOTOCHEMISTRY AND SYNTHESIS OF STEREOISOMERS OF VITAMIN-A
    LIU, RSH
    ASATO, AE
    [J]. TETRAHEDRON, 1984, 40 (11) : 1931 - 1969