Tandem radical cyclization-based strategy for the synthesis of oxa- and aza-cages: a case of fragmentation versus cyclization

被引：11
|
作者：
Gharpure, Santosh J. [1 ]
Porwal, Suheel K. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India
来源：
TETRAHEDRON LETTERS | 2010年 / 51卷 / 25期
关键词：
TETRAACETAL TETRAOXA-CAGES; SOLID-STATE; STEREOSELECTIVE-SYNTHESIS; HYDRIDE REARRANGEMENT; CRYSTAL-STRUCTURE; ACETAL GROUP; BOWLS; CHEMISTRY; CONSTRUCTION; ARCHITECTURE;
D O I：
10.1016/j.tetlet.2010.04.081
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new strategy for the synthesis of oxa- and aza-cage compounds based on tandem radical cyclizations is described. The iodides 1 lead to oxa-cages 3 after two tandem radical cyclizations. The ester 10aa on reaction with n-Bu3SnH and AIBN gives rise to the oxa-cage 12aa after two tandem 5-exo-trig cyclizations. On the other hand, reaction of the ketones 17aa and 21 under similar conditions furnished the oxa-cages 20aa and 23, respectively, via a double 5-exo-trig tandem radical cyclization followed by fragmentation. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3324 / 3329
页数：6
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    Niranjana, P.
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    [J]. ORGANIC LETTERS, 2012, 14 (21) : 5476 - 5479
  • [3] Cascade Radical Cyclization to Vinylogous Carbonates/Carbamates for the Synthesis of Oxa- and Aza-Angular Triquinanes: Diastereoselectivity Depends on the Ring Size of Radical Precursor
    Gharpure, Santosh J.
    Niranjana, P.
    Porwal, Suheel K.
    [J]. SYNTHESIS-STUTTGART, 2018, 50 (15): : 2954 - 2967
  • [4] Total Synthesis of Clavilactone B: A Radical Cyclization Fragmentation Strategy
    Suizu, Hiroshi
    Shigeoka, Daisuke
    Aoyama, Hiroshi
    Yoshimitsu, Takehiko
    [J]. ORGANIC LETTERS, 2015, 17 (01) : 126 - 129
  • [5] Stereoselective synthesis of new oxa-cages via alkyl radical cyclization to vinylogous carbonates
    Gharpure, Santosh J.
    Porwal, Suheel Kumar
    [J]. SYNLETT, 2008, (02) : 242 - 246
  • [6] Total Synthesis of Potent Antitumor Macrolide (-)-Zampanolide: An Oxidative Intramolecular Cyclization-Based Strategy
    Ghosh, Arun K.
    Cheng, Xu
    Bai, Ruoli
    Hamel, Ernest
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 2012 (22) : 4130 - 4139
  • [7] Cyclization/alkoxy radical fragmentation tandem: An efficient approach to the synthesis of bridged cyclooctane derivatives
    [J]. Journal of the Serbian Chemical Society, 1997, 62 (09): : 727 - 735
  • [8] A TANDEM DIELS-ALDER RADICAL CYCLIZATION STRATEGY FOR THE SYNTHESIS OF POLYCYCLIC SYSTEMS
    GHOSH, T
    HART, H
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1988, 195 : 418 - ORGN
  • [9] A Novel Synthesis of (-)-Huperzine A via Tandem Intramolecular Aza-Prins Cyclization-Cyclobutane Fragmentation
    White, James D.
    Li, Yang
    Kim, Jungchul
    Terinek, Miroslav
    [J]. ORGANIC LETTERS, 2013, 15 (04) : 882 - 885
  • [10] Chemoenzymatic synthesis of the morphine skeleton: Stepwise versus tandem radical cyclization.
    Butora, G
    Hudlicky, T
    Gum, AG
    Fearnley, SP
    Stabile, MR
    Abboud, KA
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 27 - ORGN
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