Chemical synthesis of optically active cis-cyclohexa-3,5-diene-1,2-diols and their 5-2H-derivatives

被引：10
作者：
Hanazawa, T [1 ]
Okamoto, S [1 ]
Sato, F [1 ]
机构：
[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 32期
关键词：
cis-cyclohexane-3,5-dien-1,2-diol; optically active; chemical synthesis; deuterium;
D O I：
10.1016/S0040-4039(01)01014-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A variety of optically active 3-substituted cis-cyclohexane-3,5-dien-1,2-diol acetonides were readily prepared from chiral 5-(tert-butyldimethylsilyloxy)-2-cyclohexenone through a seven-step reaction in good overall yield. The synthesis also allowed preparation of the acetonide having an H-2-atom at the 5-position. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：5455 / 5457
页数：3
相关论文
共 17 条
  • [1] Desymmetrization of cyclohexadienylsilanes. Regio-, diastereo-, and enantioselective access to sugar mimics
    Angelaud, R
    Babot, O
    Charvat, T
    Landais, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (26) : 9613 - 9624
  • [2] Chemoenzymatic synthesis of arene oxides and trans-dihydrodiols from cis-dihydrodiols of monosubstituted benzenes
    Boyd, DR
    Sharma, ND
    Dalton, H
    Clarke, DA
    [J]. CHEMICAL COMMUNICATIONS, 1996, (01) : 45 - 46
  • [3] Brown S.M., 1993, ORGANIC SYNTHESIS TH, V2, P113
  • [4] THE USE OF CYCLOHEXA-3,5-DIENE-1,2-DIOLS IN ENANTIOSPECIFIC SYNTHESIS
    CARLESS, HAJ
    [J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (07) : 795 - 826
  • [5] OXIDATION OF BIPHENYL BY A BEIJERINCKIA SPECIES
    GIBSON, DT
    ROBERTS, RL
    WELLS, MC
    KOBAL, VM
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1973, 50 (02) : 211 - 219
  • [6] Asymmetric synthesis of palitantin from the (5R)-tert-butyldimethylsiloxy-2-cyclohexenone
    Hareau, G
    Koiwa, M
    Hanazawa, T
    Sato, F
    [J]. TETRAHEDRON LETTERS, 1999, 40 (42) : 7493 - 7496
  • [7] Asymmetric synthesis of 1α,25-dihydroxyvitamin D3 A-ring precursor starting with 5-tert-butyldimethylsiloxy-2-cyclohexenone
    Hareau, GPJ
    Koiwa, M
    Sato, F
    [J]. TETRAHEDRON LETTERS, 2000, 41 (14) : 2385 - 2388
  • [8] Synthesis of optically active 5-(tert-butyldimethylsiloxy)-2-cyclohexenone and its 6-substituted derivatives as useful chiral building blocks for the synthesis of cyclohexane rings.: Syntheses of carvone, penienone, and penihydrone
    Hareau, GPJ
    Koiwa, M
    Hikichi, S
    Sato, F
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (15) : 3640 - 3650
  • [9] Hareau-Vittini G, 1998, ANGEW CHEM INT EDIT, V37, P2099, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2099::AID-ANIE2099>3.0.CO
  • [10] 2-U
12