Asymmetric total synthesis of (+)-carneic acid A and structure revision of its natural form

被引:10
|
作者
Yamakoshi, Shuhei [1 ]
Hayashi, Nobuyuki [1 ]
Suzuki, Takahiro [1 ]
Nakada, Masahisa [1 ]
机构
[1] Waseda Univ, Fac Sci & Engn, Dept Chem & Biochem, Shinjuku Ku, Tokyo 1698555, Japan
关键词
(+)-PHOMOPSIDIN; OXIDATION; REAGENTS;
D O I
10.1016/j.tetlet.2009.07.024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This Letter describes the asymmetric total synthesis of (+)-carneic acid A via the stereoselective IMDA reaction of (E,E,E)-triene, which was prepared from the commercially available methyl (S)-3-hydroxy-2-methylpropionate. By this asymmetric total synthesis, we verified that the reported absolute structure of naturally occurring carneic acid A must be revised. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5372 / 5375
页数:4
相关论文
共 50 条
  • [31] Asymmetric total synthesis of antiochic acid
    Zhao, Yu-Jun
    Loh, Teck-Peng
    ORGANIC LETTERS, 2008, 10 (11) : 2143 - 2145
  • [32] Asymmetric total synthesis of pinnaic acid
    Xu, Shu
    Arimoto, Hirokazu
    Uemura, Daisuke
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (30) : 5746 - 5749
  • [33] AN ASYMMETRIC TOTAL SYNTHESIS OF MARTINELLIC ACID
    Badarinarayana, Vivek
    Mahmud, Hossen
    Lovely, Carl J.
    HETEROCYCLES, 2017, 95 (02) : 1082 - 1105
  • [34] The asymmetric total synthesis of (+)-salvianolic acid A
    Zheng, Yong
    Song, Wei-Bin
    Xuan, Li-Jiang
    TETRAHEDRON, 2016, 72 (33) : 5047 - 5050
  • [35] Enantioselective total synthesis of a natural hydrocarbazolone alkaloid, identification of its stereochemistry, and revision of its spectroscopic data
    Wu, Siyuan
    Harada, Shinji
    Morikawa, Takahiro
    Nishida, Atsushi
    TETRAHEDRON-ASYMMETRY, 2017, 28 (08) : 1083 - 1088
  • [36] Asymmetric total synthesis of the natural product avrainvilleol
    Wegener, Aaron
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [37] First asymmetric synthesis of the cyclohexanone subunit of baconipyrones A and B. Revision of its structure
    Turks, M
    Murcia, MC
    Scopelliti, R
    Vogel, P
    ORGANIC LETTERS, 2004, 6 (18) : 3031 - 3034
  • [38] The taumycin A macrocycle: Asymmetric total synthesis and revision of relative stereochemistry
    Maio, W. A.
    PLANTA MEDICA, 2015, 81 (11) : 859 - 859
  • [39] The Taumycin A Macrocycle: Asymmetric Total Synthesis and Revision of Relative Stereochemistry
    deGruyter, Justine N.
    Maio, William A.
    ORGANIC LETTERS, 2014, 16 (19) : 5196 - 5199
  • [40] Revision of the absolute configuration of salicylihalamide a through asymmetric total synthesis
    Wu, YS
    Esser, L
    De Brabander, JK
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2000, 39 (23) : 4308 - +