Total Synthesis of Cercidinin A via a Sequential Site-selective Acylation Strategy

被引:12
|
作者
Shibayama, Hiromitsu [1 ]
Ueda, Yoshihiro [1 ]
Kawabata, Takeo [1 ]
机构
[1] Kyoto Univ, Inst Chem Res, Uji, Kyoto 6110011, Japan
关键词
Site selectivity; Acylation; Ellagitannin; GALLIC ACID; (S)-HEXAHYDROXYDIPHENIC ACID; HEXAHYDROXYDIPHENIC ACID; GLUCOSE DERIVATIVES; ACYL; ELLAGITANNINS; CLEAVAGE; ESTERS; FUNCTIONALIZATION; CARBOHYDRATE;
D O I
10.1246/cl.190872
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Total synthesis of cercidinin A (1) was achieved in 7 overall steps from D-glucose (9 steps from gallic acid) via sequential site-selective introduction of requisite galloyl groups into hydroxy groups of unprotected glucose. No protective groups were used for hydroxy groups of D-glucose throughout the total synthesis.
引用
收藏
页码:182 / 185
页数:4
相关论文
共 50 条
  • [1] Total synthesis of conosilane A via a site-selective C-H functionalization strategy
    Yuan, Ziyun
    Hu, Xiaojun
    Zhang, Hao
    Liu, Lin
    Chen, Peng
    He, Min
    Xie, Xingang
    Wang, Xiaolei
    She, Xuegong
    CHEMICAL COMMUNICATIONS, 2018, 54 (08) : 912 - 915
  • [2] Final-stage Site-selective Acylation for the Total Synthesis of Natural Glycosides
    Ueda, Yoshihiro
    YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 2016, 136 (12): : 1631 - 1639
  • [3] Total Synthesis of Ellagitannins via Sequential Site-Selective Functionalization of Unprotected D-Glucose
    Takeuchi, Hironori
    Ueda, Yoshihiro
    Furuta, Takumi
    Kawabata, Takeo
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2017, 65 (01) : 25 - 32
  • [4] Stereo- and Site-Selective Acylation in Carbohydrate Synthesis
    Blaszczyk, Stephanie A.
    Li, Xiaolei
    Wen, Peng
    Tang, Weiping
    SYNLETT, 2024, 35 (15) : 1745 - 1762
  • [5] Design and synthesis of highly branched organocatalysts for site-selective acylation
    Ashush, Natali
    Palakuri, Ramesh
    Portnoy, Moshe
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [6] Catalyst-Controlled Site-Selective Acylation and its Application to Unconventional Total Synthesis of Natural Glycosides
    Ueda, Yoshihiro
    Kawabata, Takeo
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2020, 78 (12) : 1138 - 1150
  • [7] Catalyst-controlled site-selective acylation and its application to unconventional total synthesis of natural glycosides
    Ueda Y.
    Kawabata T.
    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2020, 78 (12): : 1138 - 1150
  • [8] Site-Selective Acylation of Pyranosides with Oligopeptide Catalysts
    Seitz, Alexander
    Wende, Raffael C.
    Roesner, Emily
    Niedek, Dominik
    Topp, Christopher
    Colgan, Avene C.
    McGarrigle, Eoghan M.
    Schreiner, Peter R.
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (05): : 3907 - 3922
  • [9] Catalytic site-selective acylation and alkylation of carbohydrates
    Tang, Weiping
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [10] Final-Stage Site-Selective Acylation for the Total Syntheses of Multifidosides A-C
    Ueda, Yoshihiro
    Furuta, Takumi
    Kawabata, Takeo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (41) : 11966 - 11970