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
来源：
TETRAHEDRON | 2014年 / 70卷 / 23期
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
  • [1] Enantioselective Synthesis of Spiroacetals via Silver(I)-Promoted Alkylation of Hemiacetals: Total Synthesis of Cephalosporolides E and F
    Chang, Stanley
    Britton, Robert
    ORGANIC LETTERS, 2012, 14 (23) : 5844 - 5847
  • [2] Total synthesis of proposed cephalosporolides H and I
    Li, Jinshan
    Zhao, Chuanfang
    Liu, Jun
    Du, Yuguo
    TETRAHEDRON, 2015, 71 (23) : 3885 - 3889
  • [3] A concise protecting-group-free synthesis of cephalosporolides E and F
    Chaudhari, Dipali A.
    Kattanguru, Pullaiah
    Fernandes, Rodney A.
    RSC ADVANCES, 2015, 5 (52): : 42131 - 42134
  • [4] A convergent synthesis of the [4.4]-spiroacetal-γ-lactones cephalosporolides E and F
    Brimble, Margaret A.
    Finch, Orla C.
    Heapy, Amanda M.
    Fraser, John D.
    Furkert, Daniel P.
    O'Connor, Patrick D.
    TETRAHEDRON, 2011, 67 (05) : 995 - 1001
  • [5] Can an n(O) → π* Interaction Provide Thermodynamic Stability to Naturally Occurring Cephalosporolides?
    Sandoval-Lira, Jacinto
    Solano-Altamirano, Juan M.
    Cortezano-Arellano, Omar
    Cruz-Gregorio, Silvano
    Meza-Leon, Rosa L.
    Hernandez-Perez, Julio M.
    Sartillo-Piscil, Fernando
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (04) : 2126 - 2132
  • [6] On the proposed structures and stereocontrolled synthesis of the cephalosporolides
    Tlais, Sami F.
    Dudley, Gregory B.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 1287 - 1292
  • [7] First total synthesis of naturally occurring (-)-nitidon and its enantiomer
    Bellina, F
    Carpita, A
    Mannocci, L
    Rossi, R
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (12) : 2610 - 2619
  • [8] Total Synthesis of (+)-Cephalosporolide E and (-)-Cephalosporolide F en route to Bassianolone
    Fernandes, Rodney A.
    Ingle, Arun B.
    SYNLETT, 2010, (01) : 158 - 160
  • [9] An efficient and enantioselective total synthesis of naturally occurring L-783277
    Choi, Hwan Geun
    Son, Jung Beom
    Park, Dong-Sik
    Ham, Young Jin
    Hah, Jung-Mi
    Sim, Taebo
    TETRAHEDRON LETTERS, 2010, 51 (38) : 4942 - 4946
  • [10] Synthesis of naturally occurring polyynes
    Shun, ALKS
    Tykwinski, RR
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (07) : 1034 - 1057
12345