Asymmetric Total Syntheses and Structure Revision of Eurotiumide A and B, and Evaluation of their Fluorescent Properties as Natural Probes

被引：0
作者：
Nakayama, Atsushi [1 ,2 ]
机构：
[1] Tokushima Univ, Inst Biomed Sci, Tokushima 7708505, Japan
[2] Tokushima Univ, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
来源：
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 2018年 / 76卷 / 05期
基金：
日本学术振兴会;
关键词：
natural product; fluorescence; anti-fouling; anti-bacterial agent; total synthesis; EPOXIDATION METHOD; N-FORMYLSACCHARIN; ACID DERIVATIVES; CO SOURCE; CARBONYLATION;
D O I：
10.5059/yukigoseikyokaishi.76.498
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric total syntheses and structure revision of dihydroisocoumarin-type natural products, eurotiumide A and eurotiumide B have been described. Key features of these total syntheses are the asymmetric Shi epoxidation, regioselective epoxide opening, and Pd-catalyzed CO insertion-lactonization cascade reaction to construct 4-methoxyisochroman-1-one skeleton. X-ray crystallographic analysis of the key intermediate revealed the absolute configuration and relative structure of eurotiumides, and it revised the reported structures of eurotiumide A and B, respectively. These natural products also exhibited highly fluorescence with several solvents with large Stokes shift.
引用
收藏
页码：498 / 501
页数：4
相关论文
共 6 条
  • [1] Dihydroisocoumarin derivatives with antifouling activities from a gorgonian-derived Eurotium sp. fungus
    Chen, Min
    Shao, Chang-Lun
    Wang, Kai-Ling
    Xu, Ying
    She, Zhi-Gang
    Wang, Chang-Yun
    [J]. TETRAHEDRON, 2014, 70 (47) : 9132 - 9138
  • [2] Formic Acid Derivatives as Practical Carbon Monoxide Surrogates for Metal-Catalyzed Carbonylation Reactions
    Konishi, Hideyuki
    Manabe, Kei
    [J]. SYNLETT, 2014, 25 (14) : 1971 - 1986
  • [3] An efficient asymmetric epoxidation method for trans-olefins mediated by a fructose-derived ketone
    Tu, Y
    Wang, ZX
    Shi, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (40) : 9806 - 9807
  • [4] Palladium-Catalyzed Fluorocarbonylation Using N-Formylsaccharin as CO Source: General Access to Carboxylic Acid Derivatives
    Ueda, Tsuyoshi
    Konishi, Hideyuki
    Manabe, Kei
    [J]. ORGANIC LETTERS, 2013, 15 (20) : 5370 - 5373
  • [5] Palladium-Catalyzed Reductive Carbonylation of Aryl Halides with N-Formylsaccharin as a CO Source
    Ueda, Tsuyoshi
    Konishi, Hideyuki
    Manabe, Kei
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (33) : 8611 - 8615
  • [6] An efficient catalytic asymmetric epoxidation method
    Wang, ZX
    Tu, Y
    Frohn, M
    Zhang, JR
    Shi, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) : 11224 - 11235
1