Azedaralide: total synthesis, relative and absolute stereochemical assignment

被引：20
|
作者：
Baker, Luke A.
Williams, Craig M. [1 ]
Bernhardt, Paul V.
Yanik, Gary W.
机构：
[1] Univ Queensland, Sch Mol & Microbial Sci, Brisbane, Qld 4072, Australia
[2] PDR Chiral Inc, Lake Park, FL 33403 USA
来源：
TETRAHEDRON | 2006年 / 62卷 / 31期
关键词：
D O I：
10.1016/j.tet.2006.05.030
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Azedaralide, a potentially advanced intermediate for the total synthesis of various tetranortriterpenes, was constructed utilising the Fernandez-Mateos protocol and assigned both relative and absolute stereochemistries. Both asymmetric aldol and classical chiral resolution attempts failed to deliver pure enantiomers whereas preparative chiral chromatography resolved racemic azedaralide with ease. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7355 / 7360
页数：6
相关论文
共 50 条
  • [1] Total Synthesis and Absolute Stereochemical Assignment of Kibdelone C
    Sloman, David L.
    Bacon, Jeffrey W.
    Porco, John A., Jr.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) : 9952 - 9955
  • [2] Total Synthesis and Absolute Stereochemical Assignment of (-)-Communesin F
    Zuo, Zhiwei
    Xie, Weiqing
    Ma, Dawei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13226 - 13228
  • [3] Total synthesis and absolute stereochemical assignment of (+)- and (-)-galbulimima alkaloid 13
    Movassaghi, Mohammad
    Hunt, Diana K.
    Tjandra, Meiliana
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (25) : 8126 - 8127
  • [4] TOTAL SYNTHESIS AND ABSOLUTE STEREOCHEMICAL ASSIGNMENT OF GILVOCARCIN-M
    MATSUMOTO, T
    HOSOYA, T
    SUZUKI, K
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) : 3568 - 3570
  • [5] Total Synthesis and Absolute Stereochemical Assignment of Microgrewiapine A and Its Stereoisomers
    Macha, Lingamurthy
    Ha, Hyun-Joon
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (01): : 94 - 103
  • [6] Potentially Biomimetic Total Synthesis and Relative Stereochemical Assignment of (±)-Gracilamine
    Tian, Songchuan
    Zi, Weiwei
    Ma, Dawei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (40) : 10141 - 10144
  • [7] Callipeltoside A: Assignment of absolute and relative configuration by total synthesis
    Trost, BM
    Dirat, O
    Gunzner, JL
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (05) : 841 - +
  • [8] Total synthesis of (+)-apiosporamide: Assignment of relative and absolute configuration
    Williams, DR
    Kammler, DC
    Donnell, AF
    Goundry, WRF
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (41) : 6715 - 6718
  • [9] Synthesis and absolute stereochemical assignment of (+)-miyakolide
    Evans, DA
    Ripin, DHB
    Halstead, DP
    Campos, KR
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) : 6816 - 6826
  • [10] Total Synthesis and Stereochemical Assignment of (-)-Ushikulide A
    Trost, Barry M.
    O'Boyle, Brendan M.
    Hund, Daniel
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (41) : 15061 - 15074
12345