Total synthesis of naturally occurring cephalosporolides E/F

被引:21
|
作者
Kona, Chandrababu Naidu [1 ]
Ramana, C. V. [1 ]
机构
[1] CSIR, Div Organ Chem, Natl Chem Lab, Pune 411008, Maharashtra, India
关键词
Cephalosporolide; Epoxide-alkyne coupling; Gold catalysis; Alkynetetrol; Spiroketalization; MARINE-DERIVED FUNGUS; HIGHLY EFFICIENT ACCESS; MEDIATED CYCLOISOMERIZATION; SPIROKETALS; ALKYNES; LACTONES; ALCOHOLS; CYCLIZATIONS; HETEROCYCLES; PRODUCTS;
D O I
10.1016/j.tet.2014.04.026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A modular total synthesis of cephalosporolides E/F featuring sequential epoxide-alkyne coupling and subsequent highly regioselective gold catalyzed alkynolcycloisomerizatio of the resulting alkynetetrol to construct the central spiroketal core has been documented. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3653 / 3656
页数:4
相关论文
共 50 条
  • [31] Englerin, a naturally occurring sesquiterpene diester: Isolation, synthesis and biological relevance
    Sewariya, Shubham
    Singh, Snigdha
    Rana, Natasha
    Kumar, Yogesh
    Chandra, Ramesh
    Anderson, Edward A.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY REPORTS, 2023, 7
  • [32] Total synthesis of (-)-amathaspiramide F
    Sakaguchi, Kazuhiko
    Ayabe, Miki
    Watanabe, Yusuke
    Okada, Takuya
    Kawamura, Kazushige
    Shinada, Tetsuro
    Ohfune, Yasufumi
    TETRAHEDRON, 2009, 65 (50) : 10355 - 10364
  • [33] TOTAL SYNTHESIS OF (+)-HETEROPLEXISOLIDE E
    Kutsumura, Noriki
    Kiriseko, Akito
    Saito, Takao
    HETEROCYCLES, 2012, 86 (02) : 1367 - 1378
  • [34] (-)-Isoscopariusin A, a Naturally Occurring Immunosuppressive Meroditerpenoid: Structure Elucidation and Scalable Chemical Synthesis
    Yan, Bing-Chao
    Zhou, Min
    Li, Jian
    Li, Xiao-Nian
    He, Shi-Jun
    Zuo, Jian-Ping
    Sun, Han-Dong
    Li, Ang
    Puno, Pema-Tenzin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (23) : 12859 - 12867
  • [35] An efficient organocatalytic route for asymmetric total synthesis of Stagonolide F
    Shelke, Anil M.
    Suryavanshi, Gurunath
    TETRAHEDRON LETTERS, 2015, 56 (45) : 6207 - 6209
  • [36] Chemical space of naturally occurring compounds
    Saldivar-Gonzalez, Fernanda, I
    Angelica Pilon-Jimenez, B.
    Medina-Franco, Jose L.
    PHYSICAL SCIENCES REVIEWS, 2019, 4 (05)
  • [37] α,β-Dehydroamino acids in naturally occurring peptides
    Siodlak, Dawid
    AMINO ACIDS, 2015, 47 (01) : 1 - 17
  • [38] Mercuric triflate-3TMU catalyzed cyclization of ω-alkynoic acids and synthesis of a naturally occurring γ-methylene-γ-lactone
    Imagawa, H
    Fujikawa, Y
    Tsuchihiro, A
    Kinoshita, A
    Yoshinaga, T
    Takao, H
    Nishizawa, M
    SYNLETT, 2006, (04) : 639 - 641
  • [39] α,β-Dehydroamino acids in naturally occurring peptides
    Dawid Siodłak
    Amino Acids, 2015, 47 : 1 - 17
  • [40] A Carbohydrate Approach for the First Total Synthesis of Cochliomycin C: Stereoselective Total Synthesis of Paecilomycin E, Paecilomycin F and 6′-epi-Cochliomycin C
    Mahankali, Bakkolla
    Srihari, Pabbaraja
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (18) : 3983 - 3993