Eleuthesides and their analogs: IV. Synthesis of (1R,5R,6S)-6-(1,3-dithian-2-yl)-1-(2-hydroxyethyl)-5-methylcyclohex-3-ene and its O-tert-butyldimethylsilyl derivative

被引:7
作者
Sharipov, B. T. [1 ]
Pershin, A. A. [1 ]
Pilipenko, A. N. [1 ]
Salikhov, Sh. M. [1 ]
Valeev, F. A. [1 ]
机构
[1] Russian Acad Sci, Inst Organ Chem, Ufa Res Ctr, Ufa 450054, Bashkortostan, Russia
基金
俄罗斯基础研究基金会;
关键词
LEVOGLUCOSENONE ADDUCT; RED-AL; ISOPRENE;
D O I
10.1134/S1070428013100060
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two schemes for the preparation of chiral alcohols as key synthons for the synthesis of eleutheside analog at the A ring have been developed on the basis of the Diels-Alder adduct of levoglucosenone with piperylene.
引用
收藏
页码:1437 / 1446
页数:10
相关论文
共 10 条
  • [1] Broek S.A.M.W., 2010, EUR J ORG CHEM, P5906
  • [2] Eleuthesides and their analogs: III. Reaction of Red-Al with γ,δ-epoxy nitriles
    Khalilova, Yu. A.
    Doronina, O. Yu.
    Sharipov, B. T.
    Spirikhin, L. V.
    Valeev, F. A.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 49 (07) : 986 - 994
  • [3] Eleuthesides and their analogs: II. Side chain construction in the A ring. Specific action of Red-Al
    Khalilova, Yu. A.
    Krasnoslobodtseva, O. Yu.
    Sharipov, B. T.
    Spirikhin, L. V.
    Valeev, F. A.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 48 (04) : 513 - 518
  • [4] Improved procedure for the reductive acetylation of acyclic esters and a new synthesis of ethers
    Kopecky, DJ
    Rychnovsky, SD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (01) : 191 - 198
  • [5] Reactions of stereocontrolled intramolecular carbocyclization of levoglucosenone adduct with isoprene
    Sharipov, B. T.
    Krasnoslobodtseva, O. Yu
    Spirikhin, L. V.
    Valeev, F. A.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (02) : 226 - 235
  • [6] Cleavage of the 1,6-anhydro bridge in the levoglucosenone adduct with isoprene and its derivatives
    Sharipov, B. T.
    Krasnoslobodtseva, O. Yu.
    Spirikhin, L. V.
    Valeev, F. A.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (01) : 129 - 137
  • [7] Nucleophilic additions to fused bicyclic five-membered ring oxocarbenium ions: Evidence for preferential attack on the inside face
    Smith, DM
    Tran, MB
    Woerpel, KA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (46) : 14149 - 14152
  • [8] VALEEV FA, 1993, ZH ORG KHIM+, V29, P205
  • [9] VALEEV FA, 1996, IZV ROSS ACAD NAUK K, P2584
  • [10] TOTAL SYNTHESES OF (+/-)-SEYCHELLENE, (+/-)-ISOCYCLOSEYCHELLENE, AND (+/-)-ISOSEYCHELLENE
    WELCH, SC
    CHOU, CY
    GRUBER, JM
    ASSERCQ, JM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (15) : 2668 - 2676