Total syntheses of (±)-musellarins A-C

被引:26
|
作者
Li, Zhilong [1 ]
Leung, Tsz-Fai [1 ]
Tong, Rongbiao [1 ]
机构
[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China
关键词
DE-NOVO SYNTHESIS; CATALYZED GLYCOSYLATION REACTION; FRIEDEL-CRAFTS CYCLIZATION; DIAZONIUM SALTS; NORHALICHONDRIN-B; HECK ARYLATION; METHYL-ESTER; PALLADIUM; REDUCTION; DERIVATIVES;
D O I
10.1039/c4cc05248j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first, diastereoselective total syntheses of musellarins A-C were achieved concisely with 7.8-9.8% yields in 15-16 steps. The key synthetic features include (i) an Achmatowicz rearrangement, Kishi reduction, and Friedel-Crafts cyclization to construct the tricyclic framework and (ii) Heck coupling of aryldiazonium salts to introduce the aryl group into the dihydropyran in a 2,6-trans fashion in the final stage of synthesis.
引用
收藏
页码:10990 / 10993
页数:4
相关论文
共 50 条
  • [31] Solid-phase syntheses of Loloatins A-C
    Scherkenbeck, J
    Chen, HR
    Haynes, RK
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (14) : 2350 - 2355
  • [32] Stereodivergent and enantioselective total syntheses of isochaetominines A-C and four pairs of isochaetominine C enantiomers: a six-step approach
    Mao, Zhong-Yi
    Geng, Hui
    Zhang, Tian-Tian
    Ruan, Yuan-Ping
    Ye, Jian-Liang
    Huang, Pei-Qiang
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (01): : 24 - 37
  • [33] Total synthesis of pyrophen and campyrones A-C
    Reber, Keith
    Burdge, Hannah
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [34] Total synthesis of cyclodepsipeptide Hikiamides A-C
    Fu Donglin
    Rao Xuemin
    Xu Jinyi
    Xie Weijia
    Wu Xiaoming
    JOURNAL OF CHINA PHARMACEUTICAL UNIVERSITY, 2018, 49 (02) : 181 - 186
  • [35] Total Synthesis of Pyrophen and Campyrones A-C
    Reber, Keith P.
    Burdge, Hannah E.
    JOURNAL OF NATURAL PRODUCTS, 2018, 81 (02): : 292 - 297
  • [36] Bioinspired total synthesis of boneratamides A-C
    Ooka, Kaito
    Nakanishi, Keisuke
    Udagawa, Yutaro
    Ichikawa, Yoshiyasu
    Hosokawa, Seijiro
    Organic and Biomolecular Chemistry, 2022, 20 (42): : 8236 - 8242
  • [37] Enantioselective total synthesis of valeriananoids A-C
    Srikrishna, A
    Satyanarayana, G
    ORGANIC LETTERS, 2004, 6 (14) : 2337 - 2339
  • [38] Total Synthesis of Pyrophen and Campyrones A-C
    Burdge, Hannah
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [39] Collective Total Synthesis of (-)-Lundurines A-C
    Xu, Wei
    Zhao, Jianfei
    Tao, Cheng
    Wang, Huifei
    Li, Yun
    Cheng, Bin
    Zhai, Hongbin
    ORGANIC LETTERS, 2018, 20 (06) : 1509 - 1512
  • [40] Total Synthesis of Spiroalkaloids Lycibarbarines A-C
    Nie, Pengpeng
    Zhao, Chuanfang
    Yu, Shuai
    Liu, Jun
    Du, Yuguo
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (33)