Synthesis of bicyclic lactones via I2-mediated intramolecular tandem C-C/C-O bond formation

被引:6
|
作者
Maejima, Saki [1 ]
Osuka, Mai [1 ]
Yamaguchi, Eiji [1 ]
Itoh, Akichika [1 ]
机构
[1] Gifu Pharmaceut Univ, 1-25-4 Daigaku Nishi, Gifu 5011196, Japan
关键词
Lactones; Polycyclic compounds; Cyclization; C-C bond formation; Molecular iodine; ASYMMETRIC IODOCARBOCYCLIZATION REACTION; OXIDATIVE RADICAL CYCLIZATIONS; MANGANESE(III) ACETATE; EFFICIENT STRATEGY; MOLECULAR-IODINE; GAMMA-LACTONES; ACID; DERIVATIVES; PRECURSORS; ALKENES;
D O I
10.1016/j.tet.2018.04.081
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The iodine/DMAP-mediated intramolecular tandem C-C/C-O bond forming reaction of malonate bearing alkene moiety proceeded to give bicyclic lactones with good diastereoselectivity in good yield. The mechanistic investigation was also discussed on the basis of various control experimental results. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2985 / 2990
页数:6
相关论文
共 50 条
  • [1] I2-Mediated Oxidative C-O Bond Formation for the Synthesis of Isoxazoles
    Hou, Jiao
    Zhang, Xinting
    Yu, Wenquan
    Chang, Junbiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (12) : 3236 - 3241
  • [2] Synthesis of β-Nitroamines and α-Aminonitriles by I2-Mediated Oxidative C-C Bond Formation
    Li, Qianmin
    Wang, Manman
    Yu, Wenquan
    Chang, Junbiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (11) : 3966 - 3976
  • [3] AN ENANTIOSELECTIVE SYNTHESIS OF N-METHYLFUCOSAMINE VIA TANDEM C-C/C-O BOND FORMATION
    SAMES, D
    POLT, R
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 392 - ORGN
  • [4] AN ENANTIOSELECTIVE SYNTHESIS OF N-METHYLFUCOSAMINE VIA TANDEM C-C C-O BOND FORMATION
    SAMES, D
    POLT, R
    JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (16): : 4596 - 4601
  • [5] One-pot C-C/C-O bond formation: synthesis of spirocyclic lactones
    Niharika, Pedireddi
    Satyanarayana, Gedu
    RSC ADVANCES, 2016, 6 (02): : 837 - 843
  • [6] Benzyl (phenyl) γ- and δ-lactones via photoinduced tandem Ar-C, C-O bond formation
    Protti, Stefano
    Fagnoni, Maurizio
    Albini, Angelo
    Journal of the American Chemical Society, 2006, 128 (33): : 10670 - 10671
  • [7] Benzyl (phenyl) γ- and δ-lactones via photoinduced tandem Ar-C, C-O bond formation
    Protti, Stefano
    Fagnoni, Maurizio
    Albini, Angelo
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (33) : 10670 - 10671
  • [8] Formal Total Synthesis of Brevisamide by Using a Tandem Isomerization/C-O and C-C Bond Formation Reaction
    Banoth, Shivalal
    Maity, Saurabh
    Kumar, Sudheer R.
    Yadav, J. S.
    Mohapatra, Debendra K.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (13) : 2300 - 2307
  • [9] NEW METHODS OF C-C AND C-O BOND FORMATION IN THE SYNTHESIS OF CONJUGATED POLYMERS
    KLAPPER, M
    MULLEN, K
    MACROMOLECULAR SYMPOSIA, 1995, 98 : 233 - 246
  • [10] Stereoselective synthesis of (+)-decarestrictine L using tandem isomerization followed by C-O and C-C bond formation reaction
    Banoth, Shivalal
    Kanikarapu, Suresh
    Yadav, Jhillu S.
    Mohapatra, Debendra K.
    TETRAHEDRON LETTERS, 2016, 57 (39) : 4368 - 4370