Various synthetic approaches for [6,7,m]-tricyclic compounds containing an oxygen-bridged skeleton

被引:0
作者
Kang, Juyeon
Oh, Chang Ho [1 ,2 ]
机构
[1] Hanyang Univ, Dept Chem, Seoul 04763, South Korea
[2] Hanyang Univ, Res Inst Nat Sci, Seoul 04763, South Korea
基金
新加坡国家研究基金会;
关键词
6; 7; m]-tricyclic compound; Au catalyst; iodine; oxacyclic compound; oxygen; PLATINUM-CATALYZED CYCLIZATION; CONTAINING CARBONYL YLIDES; ELECTROPHILIC CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; TANDEM; CYCLOADDITION; GENERATION; INSERTION; ACCESS;
D O I
10.1002/bkcs.12642
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report the synthesis of [6,7,5]-tricyclic compounds containing an oxabicyclo [3.2.1] octane system from 1,6-enyne carbonyl. We also synthesized [6,7,6]-tricyclic compound from 1,7-enyne carbonyl through Au-catalyzed cyclization. The synthesis of oxacyclic compounds using iodine or oxygen is environmentally friendly cyclization methods. Oxacyclic compounds are useful for synthesizing various diterpene alkaloids.
引用
收藏
页码:163 / 167
页数:5
相关论文
共 41 条
  • [1] A simple, two-step synthesis of 3-iodoindoles
    Amjad, M
    Knight, DW
    [J]. TETRAHEDRON LETTERS, 2004, 45 (03) : 539 - 541
  • [2] A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions
    Arcadi, A
    Cacchi, S
    Fabrizi, G
    Marinelli, F
    Moro, L
    [J]. SYNLETT, 1999, (09) : 1432 - 1434
  • [3] The taxane diterpenoids
    Baloglu, E
    Kingston, DGI
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (10): : 1448 - 1472
  • [4] Gold-Catalyzed Reaction of ortho-Alkynylarylaldehydes with Conjugated Dienes: An Efficient Access to Highly Strained Tetracyclic Bridgehead Olefins
    Cao, Ziping
    Zhu, Hongbo
    Meng, Xin
    Tian, Laijin
    Sun, Xuejun
    Chen, Guang
    You, Jinmao
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (27) : 9125 - 9129
  • [5] Donor- and acceptor-enynals/enynones
    Chen, Lianfen
    Liu, Zhili
    Zhu, Shifa
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (46) : 8884 - 8898
  • [6] PHOTOCHEMICAL ACTIVATION OF ALPHA-BETA-EPOXYKETONES - FORMATION OF BENZANNELATED PERHYDROAZULENES BY INTRAMOLECULAR TRAPPING OF A REACTIVE INTERMEDIATE
    FELDMAN, KS
    [J]. TETRAHEDRON LETTERS, 1983, 24 (50) : 5585 - 5586
  • [7] Natural sesquiterpenoids
    Fraga, BM
    [J]. NATURAL PRODUCT REPORTS, 2005, 22 (04) : 465 - 486
  • [8] Towards a general diastereoselective route to oxabicyclo[3.2.1]octanes via a gold-catalysed cascade reaction
    Fu, Junkai
    Gu, Yueqing
    Yuan, Hao
    Luo, Tuoping
    Liu, Song
    Lan, Yu
    Gong, Jianxian
    Yang, Zhen
    [J]. NATURE COMMUNICATIONS, 2015, 6
  • [9] Grob T., 2013, CHEM-EUR J, V19, P14787
  • [10] Gold catalysis:: Mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects
    Hashmi, ASK
    Weyrauch, JP
    Frey, W
    Bats, JW
    [J]. ORGANIC LETTERS, 2004, 6 (23) : 4391 - 4394