A Flexible Approach to 6,5-Benzannulated Spiroketals

被引：14
|
作者：
Wilson, Zoe E. [1 ]
Hubert, Jonathan G. [1 ]
Brimble, Margaret A. [1 ]
机构：
[1] Univ Auckland, Dept Chem, Auckland, New Zealand
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 20-21期
关键词：
Spiroketals; Olefination; Hydrogenation; Cyclisation; Synthetic methods; PRODUCT-LIKE SCAFFOLDS; BIOLOGICAL-ACTIVITY; CHEMICAL VARIATION; CONVERGENT ROUTE; PURPUROMYCIN; RUBROMYCINS; DESIGN;
D O I：
10.1002/ejoc.201100345
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel route to simple 6,5-benzannulated spiroketal analogues has been developed. A convergent Horner-Wadsworth-Emmons olefination enabled ready assembly of the spiroketal precursors. Use of a benzyl protecting group strategy enabled an efficient one-pot hydrogenation/deprotection/spiroketalisation process to be employed providing a robust method to access a range of substituted aromatic monobenzannulated spiroketals.
引用
收藏
页码：3938 / 3945
页数：8
相关论文
共 50 条
  • [1] De Novo Synthesis of Tricyclic 5,5-Benzannulated Spiroketals
    Rao, Maddali L. N.
    Islam, Sk Shamim
    ORGANIC LETTERS, 2021, 23 (10) : 3944 - 3948
  • [2] Benzannulated 6,5-Spiroketals from Donor-Acceptor Cyclopropanes
    Gai, Sinan
    Lucas, Nigel T.
    Hawkins, Bill C.
    ORGANIC LETTERS, 2019, 21 (08) : 2872 - 2875
  • [3] A Diels-Alder approach to benzannulated [5,6]-spiroketals
    Bray, C.D.
    Synthesis, 2009, (11)
  • [4] Photoinduced Synthesis of Benzannulated Spiroketals
    Chen, Xinzheng
    Wang, Sasa
    SYNLETT, 2015, 26 (14) : 2042 - 2046
  • [5] Expedient synthesis of [5,5]- and [6,5]-benzannulated spiroketals from 1,1-diacyl-2-vinyl cyclopropanes
    Gai, Sinan
    Guilder, Holly D.
    Hawkins, Bill C.
    ARKIVOC, 2024,
  • [6] Palladium catalyzed synthesis of benzannulated steroid spiroketals
    Mayorquin-Torres, Martha C.
    Carlos Gonzalez-Orozco, Juan
    Flores-Alamo, Marcos
    Camacho-Arroyo, Ignacio
    Iglesias-Arteaga, Martin A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (04) : 725 - 737
  • [7] Synthesis of Benzannulated Spiroketals Using an Oxidative Radical Cyclization
    Sperry, Jonathan
    Liu, Yen-Cheng
    Wilson, Zoe E.
    Hubert, Jonathan G.
    Brimble, Margaret A.
    SYNTHESIS-STUTTGART, 2011, (09): : 1383 - 1398
  • [8] Chiral Squaramide Catalyzed Asymmetric Spiroketalization toward Aromatic [6,5] Spiroketals
    Roy, Tarun Kumar
    Gorad, Sachin S.
    Ghorai, Prasanta
    ORGANIC LETTERS, 2022, 24 (10) : 1889 - 1894
  • [9] Synthesis of Benzannulated [6,6]-Spiroketals by a One-Pot Carbonylative Sonogashira Coupling/Double Annulation Reaction
    Xiang, Kuirong
    Tong, Pei
    Yan, Baorun
    Long, Lingling
    Zhao, Chunbo
    Zhang, Yuan
    Li, Ying
    ORGANIC LETTERS, 2019, 21 (02) : 412 - 416
  • [10] Enantioselective access to benzannulated spiroketals using a chiral sulfoxide auxiliary
    Aitken, Harry R. M.
    Furkert, Daniel R.
    Hubert, Jonathan G.
    Wood, James M.
    Brimble, Margaret A.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (31) : 5147 - 5155
12345