A CONCISE SYNTHESIS OF (-)-CONDURITOL-F FROM L-QUEBRACHITOL VIA ALCL3-NORMAL-BU4NI MEDIATED DEMETHYLATION

被引:43
作者
AKIYAMA, T
SHIMA, H
OZAKI, S
机构
[1] Department of Applied Chemistry, Faculty of Engineering, Ehime University, Matsuyama, 790, Bunkyo-cho
关键词
(-)-CONDURITOL-F; (+)-CONDURITOL-B; L-QUEBRACHITOL; DEMETHYLATION; ALCL3;
D O I
10.1016/0040-4039(91)80092-K
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
(-)-Conduritol F was prepared starting from naturally occurring cyclitol, L-quebrachitol, in 5 steps via AlCl3-Bu4NI mediated chemoselective demethylation of the methyl ether. A preparation of (+)-conduritol B was also described.
引用
收藏
页码:5593 / 5596
页数:4
相关论文
共 27 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] DIASTEREOSELECTIVE REDUCTION OF ALPHA-KETO ESTERS BEARING CHIRO-INOSITOL DERIVATIVES AS CHIRAL AUXILIARIES
    AKIYAMA, T
    NISHIMOTO, H
    OZAKI, S
    [J]. TETRAHEDRON LETTERS, 1991, 32 (10) : 1335 - 1338
  • [3] AKIYAMA T, 1990, CHEM LETT, P1433
  • [4] ANGYAL SJ, 1963, METHODS CARBOHYDR CH, V2, P87
  • [5] CONDURITOLS AND RELATED-COMPOUNDS
    BALCI, M
    SUTBEYAZ, Y
    SECEN, H
    [J]. TETRAHEDRON, 1990, 46 (11) : 3715 - 3742
  • [6] TOTAL SYNTHESIS OF MYOINOSITOL POLYPHOSPHATES FROM BENZENE VIA CONDURITOL-B DERIVATIVES
    CARLESS, HAJ
    BUSIA, K
    [J]. TETRAHEDRON LETTERS, 1990, 31 (24) : 3449 - 3452
  • [7] TOTAL SYNTHESIS OF (-)-LAMINITOL (1D-4C-METHYL-MYO-INOSITOL) VIA MICROBIAL OXIDATION OF TOLUENE
    CARLESS, HAJ
    OAK, OZ
    [J]. TETRAHEDRON LETTERS, 1991, 32 (13) : 1671 - 1674
  • [8] TOTAL SYNTHESIS OF BENGAMIDE-E
    CHIDA, N
    TOBE, T
    OGAWA, S
    [J]. TETRAHEDRON LETTERS, 1991, 32 (08) : 1063 - 1066
  • [9] 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
  • [10] SYNTHESIS OF D-GALACTOSE AND L-GALACTOSE DERIVATIVES FROM QUEBRACHITOL
    CHIDA, N
    SUZUKI, M
    SUWAMA, M
    OGAWA, S
    [J]. JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (03) : 319 - 332