Regiospecific synthesis of polysubstituted furans and their application in organic synthesis

被引:30
|
作者
Wong, HNC
机构
[1] Department of Chemistry, Chinese University of Hong Kong, Shatin, New Territories
关键词
D O I
10.1351/pac199668020335
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The role played by 3,4-bis(trimethylsilyl)furan, 2,4-bis(trimethylsilyl)furan and 3,4-bis(tri-n-butylstannyl)furan as building blocks in the preparation of 2,3-disubstituted furans, 3,4-disubstituted furans, as well. as 2,3,5-trisubstituted furans will be summarized. The synthetic potential of furan and its polysubstituted derivatives will be illustrated by our Diels-Alder reaction deoxygenation route for the realization of several theoretically interesting benzenoid molecules, as well as by the preparation of 2-butenolides which are precursors of the naturally occurring prehispanolone, sphydrofuran and secosyrins.
引用
收藏
页码:335 / 344
页数:10
相关论文
共 50 条
  • [41] REGIOSPECIFIC SYNTHESIS OF POLYSUBSTITUTED NAPHTHALENES VIA OXAZOLINE-MEDIATED NUCLEOPHILIC AROMATIC SUBSTITUTIONS AND ADDITIONS
    GANT, TG
    MEYERS, AI
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) : 1010 - 1015
  • [42] Synthesis of polysubstituted furans by palladium-catalyzed coupling of butatrienyl carbinols with aryl halides and triflates
    Aurrecoechea, JM
    Pérez, E
    TETRAHEDRON, 2004, 60 (19) : 4139 - 4149
  • [43] GENERAL-METHOD FOR THE PREPARATION OF POLYSUBSTITUTED FURANS - NEW SYNTHESIS OF D1-MENTHOFURAN
    INOMATA, K
    NAKAYAMA, Y
    TSUTSUMI, M
    KOTAKE, H
    HETEROCYCLES, 1979, 12 (11) : 1467 - 1474
  • [44] Intermolecular tandem addition-cyclization of bromoallenes: A facile synthesis of methylenecyclopropyl carboxylates and polysubstituted Furans
    Xu, Lubin
    Huang, Xian
    Zhong, Fangrui
    ORGANIC LETTERS, 2006, 8 (22) : 5061 - 5064
  • [45] Sc(OTf)3-catalyzed synthesis of polysubstituted furans from acylacetonitriles and renewable acetol
    Huang, Wenbo
    Liu, Fang
    Wang, Kaimei
    Sidorenko, Alexander
    Bei, Maxim
    Zhang, Zhigang
    Fang, Wei
    Li, Minghao
    Gu, Yanlong
    Ke, Shaoyong
    GREEN SYNTHESIS AND CATALYSIS, 2022, 3 (04): : 380 - 384
  • [46] Electrooxidative coupling of furans and silyl enol ethers: Application to the synthesis of annulated furans
    Sperry, JB
    Whitehead, CR
    Ghiviriga, I
    Walczak, RM
    Wright, DL
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (11): : 3726 - 3734
  • [47] Synthesis of Polysubstituted Pyrroles
    Poulard, Celine
    Cornet, Julien
    Legoupy, Stephanie
    Dujardin, Gilles
    Dhal, Robert
    Huet, Francois
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (05) : 359 - 361
  • [48] SYNTHESIS ON TEMPLATES - REGIOSPECIFIC SYNTHESIS OF IMIDAZOLES
    RANGANATHAN, D
    FAROOQUI, F
    TETRAHEDRON LETTERS, 1984, 25 (49) : 5701 - 5704
  • [49] Synthesis of Polysubstituted Ferrocenesulfoxides
    Wen, Min
    Erb, William
    Mongin, Florence
    Halauko, Yury S.
    Ivashkevich, Oleg A.
    Matulis, Vadim E.
    Roisnel, Thierry
    MOLECULES, 2022, 27 (06):
  • [50] "One pot" regiospecific synthesis of polysubstituted pyrroles from benzylamines and ynones under metal free conditions
    Shen, Jinhai
    Cheng, Guolin
    Cui, Xiuling
    CHEMICAL COMMUNICATIONS, 2013, 49 (90) : 10641 - 10643