Total Synthesis of gem-Difluoromethylenated Analogues of Pironetin

被引:15
|
作者
Lin, Jing [1 ]
Yue, Xuyi [2 ]
Huang, Peng [3 ]
Cui, Daxiang [3 ]
Qing, Feng-Ling [1 ,2 ]
机构
[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[3] Shanghai Jiao Tong Univ, Inst Micro Nano Sci & Technol, Shanghai 200240, Peoples R China
来源
SYNTHESIS-STUTTGART | 2010年 / 02期
基金
中国国家自然科学基金;
关键词
pironetin; alpha; beta-unsaturated delta-lactones; gem-difluoromethylenated analogues; CHIRAL BUILDING-BLOCK; ENANTIOSELECTIVE SYNTHESIS; (-)-PIRONETIN; (-)-PA-48153C; DERIVATIVES; EFFICIENT; TUBULIN; NK10958;
D O I
10.1055/s-0029-1217099
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The straightforward synthesis of four gem-difluoromethylenated analogues of pironetin is described. Our synthesis features the efficient construction of the key intermediates through the indium-mediated gem-difluoropropargylation of aldehydes with the fluorine-containing building block.
引用
收藏
页码:267 / 275
页数:9
相关论文
共 50 条
  • [1] Synthesis of gem-difluoromethylenated analogues of boronolide
    Lin, Jing
    Qiu, Xiao-Long
    Qing, Feng-Ling
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2010, 6
  • [2] Synthesis of gem-difluoromethylenated analogues of anamarine
    Lin, Jing
    Qiu, Xiao-Long
    Qing, Feng-Ling
    JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (06) : 684 - 690
  • [3] Synthesis of gem-difluoromethylenated goniodiol
    Xie, Yang-Feng
    Xu, Xiu-Hua
    Yue, Xu-Yi
    You, Zheng-Wei
    Qing, Feng-Ling
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2008, 28 (02) : 283 - 287
  • [4] Synthesis and biological evaluation of glycosidase inhibitors:: gem-difluoromethylenated nojirimycin analogues
    Wang, Ruo-Wen
    Qiu, Xiao-Long
    Bols, Mikael
    Ortega-Caballero, Fernando
    Qing, Feng-Ling
    JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (10) : 2989 - 2997
  • [5] An efficient and general route to gem-difluoromethylenated α,β-unsaturated δ-lactones:: High enantioselective synthesis of gem-difluoromethylenated goniothalamins
    You, Zheng-Wei
    Jiang, Zhong-Xing
    Wang, Bing-Lin
    Qing, Feng-Ling
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (19): : 7261 - 7267
  • [6] Stereoselective Synthesis of gem-Difluoromethylenated Linear Azatriquinanes
    Masusai, Chonticha
    Soorukram, Darunee
    Kuhakarn, Chutima
    Reutrakul, Vichai
    Pohmakotr, Manat
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (02) : 160 - 169
  • [7] Synthesis of gem-Difluoromethylenated Polycyclic Cage Compounds
    Masusai, Chonticha
    Soorukram, Darunee
    Kuhakarn, Chutima
    Tuchinda, Patoomratana
    Pakawatchai, Chaveng
    Saithong, Saowanit
    Reutrakul, Vichai
    Pohmakotr, Manat
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (03): : 1577 - 1592
  • [8] Asymmetric Synthesis of gem-Difluoromethylenated Dihydroxypyrrolizidines and Indolizidines
    Thaharn, Watcharaporn
    Bootwicha, Teerawut
    Soorukram, Darunee
    Kuhakarn, Chutima
    Prabpai, Samran
    Kongsaeree, Palangpon
    Tuchinda, Patoomratana
    Reutrakul, Vichai
    Pohmakotr, Manat
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (19): : 8465 - 8479
  • [9] Synthesis and anticancer effect of gem-difluoromethylenated chrysin derivatives
    Zheng, Xing
    Cao, Jian Guo
    Liao, Duan Fang
    Zhu, Bing Yang
    Liu, Hui Ting
    CHINESE CHEMICAL LETTERS, 2006, 17 (11) : 1439 - 1442