TOTAL SYNTHESIS OF SIMMONDSIN

被引:23
作者
CHIDA, N [1 ]
YAMADA, K [1 ]
OGAWA, S [1 ]
机构
[1] KEIO UNIV, FAC SCI & TECHNOL, DEPT APPL CHEM, KOHOKU KU, YOKOHAMA, KANAGAWA 223, JAPAN
关键词
D O I
10.1039/c39910000588
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first total synthesis of the naturally occurring cyanoglucoside, simmondsin 1, starting from L-quebrachitol and D-glucose, is described, revealing the absolute configuration of this compound.
引用
收藏
页码:588 / 590
页数:3
相关论文
共 14 条
  • [1] CHIRAL SYNTHESIS OF D-MYO-INOSITOL 1-PHOSPHATE STARTING FROM L-QUEBRACHITOL
    AKIYAMA, T
    TAKECHI, N
    OZAKI, S
    [J]. TETRAHEDRON LETTERS, 1990, 31 (10) : 1433 - 1434
  • [2] TOTAL SYNTHESIS OF BENGAMIDE-E
    CHIDA, N
    TOBE, T
    OGAWA, S
    [J]. TETRAHEDRON LETTERS, 1991, 32 (08) : 1063 - 1066
  • [3] A FORMAL TOTAL SYNTHESIS OF (-)-ISOAVENACIOLIDE FROM L-QUEBRACHITOL
    CHIDA, N
    TOBE, T
    SUWAMA, M
    OHTSUKA, M
    OGAWA, S
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (14) : 994 - 995
  • [4] A SIMPLE ROUTE TO BETA,BETA-TREHALOSE VIA TRICHLOROACETIMIDATES
    COOK, SJ
    KHAN, R
    BROWN, JM
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1984, 3 (02) : 343 - 348
  • [5] DWUMABADU D, 1976, LLOYDIA, V39, P385
  • [6] STRUCTURE AND STEREOCHEMISTRY OF SIMMONDSIN
    ELLIGER, CA
    WAISS, AC
    LUNDIN, RE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (19) : 2930 - 2931
  • [7] SIMMONDSIN, AN UNUSUAL 2-CYANOMETHYLENECYCLOHEXYL GLUCOSIDE FROM SIMMONDSIA-CALIFORNICA
    ELLIGER, CA
    WAISS, AC
    LUNDIN, RE
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (19): : 2209 - 2212
  • [8] ON THE SELECTIVITY OF DEPROTECTION OF BENZYL, MPM (4-METHOXYBENZYL) AND DMPM (3,4-DIMETHOXYBENZYL) PROTECTING GROUPS FOR HYDROXY FUNCTIONS
    HORITA, K
    YOSHIOKA, T
    TANAKA, T
    OIKAWA, Y
    YONEMITSU, O
    [J]. TETRAHEDRON, 1986, 42 (11) : 3021 - 3028
  • [9] EFFICIENT SYNTHETIC ROUTES TO FLUORINATED ISOSTERES OF INOSITOL AND THEIR EFFECTS ON CELLULAR GROWTH
    KOZIKOWSKI, AP
    FAUQ, AH
    POWIS, G
    MELDER, DC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4528 - 4531
  • [10] PYRIDINIUM PARA-TOLUENESULFONATE - MILD AND EFFICIENT CATALYST FOR TETRAHYDROPYRANYLATION OF ALCOHOLS
    MIYASHITA, M
    YOSHIKOSHI, A
    GRIECO, PA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) : 3772 - 3774