A NEW STEREOCONTROLLED SYNTHESIS OF DIEQUATORIAL FUROFURAN LIGNANS HAVING 2 DIFFERENT ARYL GROUPS - A SYNTHESIS OF METHYL PIPERITOL

被引:29
作者
OGIKU, T [1 ]
YOSHIDA, S [1 ]
TAKAHASHI, M [1 ]
KURODA, T [1 ]
OHMIZU, H [1 ]
IWASAKI, T [1 ]
机构
[1] TANABE SEIYAKU CO LTD,DEPT SYNTHET CHEM,APPL BIOCHEM RES LAB,3-16-89 KASHIMA,YODOGAWA,OSAKA 532,JAPAN
关键词
D O I
10.1016/S0040-4039(00)60113-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Methyl piperitol, a representative example of the diequatorial furofuran lignans, was synthesized in a good overall yield based on a highly stereocontrolled tandem Michael addition-aldol reaction.
引用
收藏
页码:4473 / 4476
页数:4
相关论文
共 17 条
  • [1] ALDOL DIASTEREOSELECTION VIA ZIRCONIUM ENOLATES - PRODUCT-SELECTIVE, ENOLATE STRUCTURE INDEPENDENT CONDENSATIONS
    EVANS, DA
    MCGEE, LR
    [J]. TETRAHEDRON LETTERS, 1980, 21 (41) : 3975 - 3978
  • [2] TRANSIENT TITANIUM ENOLATE ALDOL CONDENSATIONS
    HARRISON, CR
    [J]. TETRAHEDRON LETTERS, 1987, 28 (36) : 4135 - 4138
  • [3] NEW INVESTIGATION ON SASSAFRAS ROOT
    HOKE, M
    HANSEL, R
    [J]. ARCHIV DER PHARMAZIE UND BERICHTE DER DEUTSCHEN PHARMAZEUTISCHEN GESSELSCHAFT, 1972, 305 (01): : 33 - &
  • [4] ANODIC-OXIDATION OF 4-HYDROXYCINNAMIC ACIDS
    IGUCHI, M
    NISHIYAMA, A
    ETO, H
    TERADA, Y
    YAMAMURA, S
    [J]. CHEMISTRY LETTERS, 1979, (11) : 1397 - 1400
  • [5] JANSEN JFG, 1991, TETRAHEDRON LETT, V32, P2339
  • [6] A NEW METHOD FOR GENERATION OF 4-ARYL AND 6-ARYL THIENO[2,3-C]FURANS, AND 3-ARYL FURO[3,4-B]PYRIDINE
    KURODA, T
    TAKAHASHI, M
    OGIKU, T
    OHMIZU, H
    KONDO, K
    IWASAKI, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (22) : 1635 - 1636
  • [7] TRANSITION STRUCTURES OF ALDOL REACTIONS
    LI, Y
    PADDONROW, MN
    HOUK, KN
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) : 3684 - 3686
  • [8] BIOLOGICAL-ACTIVITIES OF LIGNANS
    MACRAE, WD
    TOWERS, GHN
    [J]. PHYTOCHEMISTRY, 1984, 23 (06) : 1207 - 1220
  • [9] MORITANI Y, 1990, TETRAHEDRON LETT, V31, P3615
  • [10] A NEW 2-STEP SYNTHESIS OF 1-ARYLNAPHTHALENE LIGNANS FROM CYANOHYDRINS
    OGIKU, T
    SEKI, M
    TAKAHASHI, M
    OHMIZU, H
    IWASAKI, T
    [J]. TETRAHEDRON LETTERS, 1990, 31 (38) : 5487 - 5490