Synthesis of Atromentin and Its O-Alkylated Natural Products

被引:11
作者
Ye, Yue Qi [1 ,2 ]
Koshino, Hiroyuki [1 ]
Abe, Naoki [2 ]
Nakamura, Takemichi [1 ]
Hashizume, Daisuke [1 ]
Takahashi, Shunya [1 ]
机构
[1] RIKEN, Wako, Saitama 3510198, Japan
[2] Tokyo Univ Agr, Fac Appl Biosci, Dept Nutr Sci, Setagaya Ku, Tokyo 1568502, Japan
关键词
terphenyl; atromentin; single-crystal X-ray analysis; Suzuki-Miyaura coupling; DERIVATIVES;
D O I
10.1271/bbb.100451
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The structure of a long-known natural pigment, atromentin, was established by a total synthesis based on double Suzuki-Miyaura coupling and by a single-crystal X-ray analysis of the synthetic sample thereby obtained. A similar strategy including ceric ammonium nitrate (CAN) oxidation was applied to prepare 2-O-methoxyatromentin and thelephantin I.
引用
收藏
页码:2342 / 2344
页数:3
相关论文
共 50 条
  • [21] Natural products inspired synthesis of neuroprotective agents against H2O2-induced cell death
    Almaliti, Jehad
    Nada, Shadia E.
    Carter, Bryaune
    Shah, Zahoor A.
    Tillekeratne, L. M. Viranga
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (05) : 1232 - 1237
  • [22] Total Synthesis of Camptothecin and Related Natural Products by a Flexible Strategy
    Li, Ke
    Ou, Jinjie
    Gao, Shuanhu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (47) : 14778 - 14783
  • [23] Synthesis of the Tetracyclic Framework of Polycyclic Spiro Lignan Natural Products
    Ali, Ghada
    Cuny, Gregory D.
    ACS OMEGA, 2020, 5 (15): : 9007 - 9012
  • [24] Synthesis and antioxidant activities of benzylic bromophenols inclusive of natural products
    Bayrak, Cetin
    Uc, Eda Mehtap
    Rezaei, Mohsen
    Gulcin, Ilhami
    Menzek, Abdullah
    TURKISH JOURNAL OF CHEMISTRY, 2022, 46 (05) : 1405 - +
  • [25] Research Progress on the Synthesis of Brazilin-Type Natural Products
    Wang, Xuequan
    Liu, Wei
    Duan, Suyue
    Yang, Xiaodong
    Zhang, Hongbin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (08) : 1585 - 1597
  • [26] Synthesis of a Potent Antimalarial Agent through Natural Products Conjugation
    Bruno, Michela
    Trucchi, Beatrice
    Monti, Diego
    Romeo, Sergio
    Kaiser, Marcel
    Verotta, Luisella
    CHEMMEDCHEM, 2013, 8 (02) : 221 - 225
  • [27] Development of Biofunctional Molecules Based on Total Synthesis of Natural Products
    Hayakawa, Ichiro
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2014, 72 (02) : 126 - 136
  • [28] Applications of chiral spirocyclic phosphoric acid in the synthesis of natural products
    Yang, Fan
    2021 5TH INTERNATIONAL CONFERENCE ON ADVANCES IN ENERGY, ENVIRONMENT AND CHEMICAL SCIENCE (AEECS 2021), 2021, 245
  • [29] Conformational and Configurational Analysis in the Study and Synthesis of Chlorinated Natural Products
    Nilewski, Christian
    Geisser, Roger W.
    Ebert, Marc-Olivier
    Carreira, Erick M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (43) : 15866 - 15876
  • [30] Genomic and transcriptomic analysis of the endophytic fungus Pestalotiopsis fici reveals its lifestyle and high potential for synthesis of natural products
    Wang, Xiuna
    Zhang, Xiaoling
    Liu, Ling
    Xiang, Meichun
    Wang, Wenzhao
    Sun, Xiang
    Che, Yongsheng
    Guo, Liangdong
    Liu, Gang
    Guo, Liyun
    Wang, Chengshu
    Yin, Wen-Bing
    Stadler, Marc
    Zhang, Xinyu
    Liu, Xingzhong
    BMC GENOMICS, 2015, 16