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
  • [1] Total Syntheses of Lyconadins A-C
    Nishimura, Takuya
    Unni, Aditya K.
    Yokoshima, Satoshi
    Fukuyama, Tohru
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (08) : 3243 - 3247
  • [2] Total syntheses of trichodenones A-C
    Usami, Y
    Numata, A
    SYNLETT, 1999, (06) : 723 - 724
  • [3] Total Syntheses of Hosieines A-C
    Zhang, Jiayang
    Yan, Xu
    Zhang, Qing-Bao
    Wang, Fang
    Yang, Bin
    Yang, Yang
    ADVANCED SCIENCE, 2024, 11 (14)
  • [4] Total Syntheses of Kealiinines A-C
    Das, Jayanta
    Koswatta, Panduka B.
    Jones, J. Daniel
    Yousufuddin, Muhammed
    Lovely, Carl J.
    ORGANIC LETTERS, 2012, 14 (24) : 6210 - 6213
  • [5] Concise total syntheses of Marinoquinolines A-C
    Ni, Lijun
    Li, Ziyuan
    Wu, Fan
    Xu, Jinyi
    Wu, Xiaoming
    Kong, Lingyi
    Yao, Hequan
    TETRAHEDRON LETTERS, 2012, 53 (10) : 1271 - 1274
  • [6] Practical and Scalable Total Syntheses of (+)-Dysidavarones A-C
    Kuang, Yang
    Chang, Le
    Wang, Bingjian
    Kang, Jingyi
    Chong, Chuanke
    Lu, Zhaoyong
    SYNLETT, 2024, 35 (05) : 582 - 585
  • [7] Total syntheses of clausamines A-C and clausevatine D
    Lebold, Terry P.
    Kerr, Michael A.
    ORGANIC LETTERS, 2008, 10 (05) : 997 - 1000
  • [8] Total Syntheses of Rhodiolosides A and D and of Sachalinols A-C
    Simon, Kristina
    Jones, Peter G.
    Lindel, Thomas
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (08) : 1493 - 1503
  • [9] Enantioselective total syntheses of slagenins A-C and their antipodes
    Jiang, B
    Liu, JF
    Zhao, SY
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06): : 2376 - 2384
  • [10] First total syntheses of cytotoxic substances Russuphelins A-C
    Reddy, KL
    Vittal, TVSK
    SYNTHETIC COMMUNICATIONS, 1997, 27 (01) : 107 - 118