Total Synthesis of (+)-Dibromophakellin and (+)-Dibromophakellstatin

被引:26
作者
Imaoka, Takuya [1 ]
Akimoto, Takafumi [1 ]
Iwamoto, Osamu [1 ]
Nagasawa, Kazuo [1 ]
机构
[1] Tokyo Univ Agr & Technol, Dept Biotechnol & Life Sci, Tokyo 1848588, Japan
关键词
aminals; enamides; natural products; Overman rearrangement; total synthesis; NATURAL-PRODUCT DIBROMOPHAKELLSTATIN; PYRROLE-IMIDAZOLE ALKALOIDS; PUMMERER REACTION CHEMISTRY; AUSTRALIAN MARINE SPONGE; ENANTIOSELECTIVE SYNTHESIS; SIGMATROPIC REARRANGEMENT; STEREOSELECTIVE-SYNTHESIS; OXIDATIVE CYCLIZATION; PALAUAMINE; CORE;
D O I
10.1002/asia.201000213
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new method for the preparation of quaternary chiral aminals has been developed that employs an enamide-type Overman rearrangement process. This methodology was applied to enantioselective total syntheses of (+)-dibromo-phakellin and (+)-dibromophakellstatin.
引用
收藏
页码:1810 / 1816
页数:7
相关论文
共 50 条
  • [41] From Total Synthesis to Diverted Total Synthesis: Case Studies in the Amphidinolide Series
    Fuerstner, Alois
    ISRAEL JOURNAL OF CHEMISTRY, 2011, 51 (3-4) : 329 - 345
  • [42] Total Synthesis, Stereochemical Reassignment, and Biological Evaluation of (-)-Lyngbyaloside B
    Fuwa, Haruhiko
    Okuaki, Yuta
    Yamagata, Naoya
    Sasaki, Makoto
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (03) : 868 - 873
  • [43] Total Synthesis and Complete Stereostructure of a Marine Macrolide Glycoside, (-)-LyngbyalosideB
    Fuwa, Haruhiko
    Yamagata, Naoya
    Okuaki, Yuta
    Ogata, Yuya
    Saito, Asami
    Sasaki, Makoto
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (20) : 6815 - 6829
  • [44] Synthesis and Application of [3.3.0]Furofuranone in Total Synthesis
    Peng, Xiao-Shui
    Ylagan, Ridge Michael P.
    Siu, Yuk Ming
    Wong, Henry N. C.
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (10) : 2070 - 2083
  • [45] Enantioselective Total Synthesis of (+)-PlumisclerinA
    Gao, Ming
    Wang, Ye-Cheng
    Yang, Kai-Rui
    He, Wei
    Yang, Xiao-Liang
    Yao, Zhu-Jun
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13313 - 13318
  • [46] Total Synthesis of Maoecrystal V
    Zhang, Wei-Bin
    Lin, Guang
    Shao, Wen-Bin
    Gong, Jian-Xian
    Yang, Zhen
    CHEMISTRY-AN ASIAN JOURNAL, 2015, 10 (04) : 903 - 909
  • [47] Total Synthesis of Tulearin C
    Lehr, Konrad
    Mariz, Ronaldo
    Leseurre, Lucie
    Gabor, Barbara
    Fuerstner, Alois
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (48) : 11373 - 11377
  • [48] The Total Synthesis of Isodon Diterpenes
    Lazarski, Kiel E.
    Moritz, Benjamin J.
    Thomson, Regan J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (40) : 10588 - 10599
  • [49] Total Synthesis of Amphidinolide F
    Valot, Gaelle
    Regens, Christopher S.
    O'Malley, Daniel P.
    Godineau, Edouard
    Takikawa, Hiroshi
    Fuerstner, Alois
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (36) : 9534 - 9538
  • [50] Asymmetric Total Synthesis of Phomarol
    Fan, Jian-Hong
    Wang, Jing-Jing
    Li, Fangfang
    Wang, Guannan
    Guo, Qiang
    Chung, Lung Wa
    Li, Chuang-Chuang
    CCS CHEMISTRY, 2021, 3 (12): : 348 - 357