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
  • [31] Synthesis of the C5-C30 fragment of cyclodidemniserinol trisulfate via I2-mediated deprotection and ring closure tandem reaction
    Liu, Jian-Hua
    Jin, Yi
    Long, Ya-Qiu
    TETRAHEDRON, 2010, 66 (06) : 1267 - 1273
  • [32] I2/DMSO-mediated oxidative C-C and C-heteroatom bond formation: a sustainable approach to chemical synthesis
    Singhal, Rakshanda
    Choudhary, Satya Prakash
    Malik, Babita
    Pilania, Meenakshi
    RSC ADVANCES, 2024, 14 (09) : 5817 - 5845
  • [33] One-Pot Tandem Synthesis of 2-Arylbenzoxazole Derivatives via Copper-Catalyzed C-N and C-O Bond Formation
    Kavala, Veerababurao
    Janreddy, Donala
    Raihan, Mustafa J.
    Kuo, Chun-Wei
    Ramesh, Chintakunta
    Yao, Ching-Fa
    ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (11-12) : 2229 - 2240
  • [34] Benzyl C-O and C-N Bond Construction via C-C Bond Dissociation of Oxime Ester under Visible Light Irradiation
    Fan, Xiuwei
    Lei, Tao
    Liu, Zan
    Yang, Xiu-Long
    Cheng, Yuan-Yuan
    Liang, Ge
    Chen, Bin
    Tung, Chen-Ho
    Wu, Li-Zhu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) : 1551 - 1558
  • [35] Carbofluorination of π-Bonds and Related Reactions Involving Tandem C-C/C-F Bond Formation
    McKnight, E. Ali
    Cadwallader, Dusty
    Le, Christine M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (19)
  • [36] An effective C-C double bond formation via Cu(I)-catalyzed dehydrogenation
    Ramirez, Thomas A.
    Zhao, Baoguo
    Shi, Yian
    TETRAHEDRON LETTERS, 2010, 51 (14) : 1822 - 1825
  • [37] Cobalt catalyzed regioselective C-H methylation/acetoxylation of anilides: new routes for C-C and C-O bond formation
    Li, Ze-lin
    Wu, Peng-Yu
    Cai, Chun
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (12) : 2043 - 2047
  • [38] Metal-free one-pot synthesis of 1,3-diazaheterocyclic compounds via I2-mediated oxidative C-N bond formation
    Tian, Xianhai
    Song, Lina
    Li, Ertong
    Wang, Qiang
    Yu, Wenquan
    Chang, Junbiao
    RSC ADVANCES, 2015, 5 (76) : 62194 - 62201
  • [39] Intermolecular C-H Aminocyanation of Indoles via Copper-iodine Cocatalyzed Tandem C-N/C-C Bond Formation
    Yu, Wenhua
    Zhang, Xiaoxiang
    Liu, Chenrui
    Zhang, Yingying
    Gu, Xiaoting
    Liao, Jiahao
    Zhang, Zhuan
    Wei, Wanxing
    Li, Guanghua
    Liang, Taoyuan
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18) : 12424 - 12433
  • [40] Synthesis of 2-, 3-, and 4-Substituted Pyrido[2,3-b]indoles by C-N, C-O, and C-C(sp) Bond Formation
    Schneider, Cedric
    Goyard, David
    Gueyrard, David
    Joseph, Benoit
    Goekjian, Peter G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (34) : 6665 - 6677