Studies towards the synthesis of trocheliophorolides

被引:5
|
作者
Khomane, Navnath B. [1 ,2 ]
Meshram, Harshadas M. [3 ,4 ]
Rode, Haridas B. [1 ,2 ]
机构
[1] Indian Inst Chem Technol, CSIR, Dept Organ Synth & Proc Chem, Hyderabad 500007, Telangana, India
[2] Acad Sci & Innovat Res, New Delhi 110025, India
[3] Indian Inst Chem Technol, CSIR, Med Chem & Biotechnol Div, Hyderabad 500007, Telangana, India
[4] Meshram Life Sci Pvt Ltd, Hyderabad 500007, Telangana, India
关键词
Trocheliophorolides; Butenolides; Eglinton oxidative dimerization; Cadiot-Chodkiewicz cross coupling; Cross metathesis; CROSS-METATHESIS; NATURAL-PRODUCTS; FORMAL SYNTHESIS; BUTENOLIDES; ENANTIOMER; EFFICIENT; CIS;
D O I
10.1016/j.tetlet.2018.04.045
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Total synthesis of trocheliophorolide C epimer is reported. The synthetic strategy involves generation of lactone skeleton and preparation of unsaturated side chain followed by cross-metathesis. The Eglinton oxidative coupling, Cadiot-Chodkiewicz cross-coupling and cross-metathesis are the key reactions used in the synthesis. We also attempted the synthesis of trocheliophorolide D epimer, which includes Cu catalyzed various cross-coupling reactions. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2157 / 2160
页数:4
相关论文
共 50 条
  • [41] Studies towards the total synthesis of (+)-lophotoxin
    Walker, Johannes
    Werrel, Simon
    Donohoe, Timothy
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 252
  • [42] EPOXIDES IN SYNTHESIS - STUDIES TOWARDS THE AUROVERTINS
    FORBES, JE
    PATTENDEN, G
    TETRAHEDRON LETTERS, 1987, 28 (24) : 2771 - 2774
  • [43] STUDIES TOWARDS THE SYNTHESIS OF FREDERICAMYCIN-A
    JULIA, M
    ROLANDO, C
    VINCENT, E
    XU, JZ
    HETEROCYCLES, 1989, 28 (01) : 71 - 74
  • [44] STUDIES TOWARDS THE TOTAL SYNTHESIS OF LANKANOLIDE
    RAIMUNDO, BC
    HEATHCOCK, CH
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 210 : 47 - ORGN
  • [45] Studies towards the total synthesis of ouabagenin
    Chen, L
    Deslongchamps, P
    CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (6-7) : 728 - 740
  • [46] STUDIES TOWARDS THE SYNTHESIS OF OBTUSENYNE - SYNTHESIS OF THE HEXAHYDROOXONIN NUCLEUS
    CURTIS, NR
    HOLMES, AB
    LOONEY, MG
    TETRAHEDRON LETTERS, 1992, 33 (05) : 671 - 674
  • [47] STUDIES DIRECTED TOWARDS SYNTHESIS OF FOMANNOSIN - SYNTHESIS OF (+/-)-DIHYDROFOMANNOSIN ACETATE
    KOSUGI, H
    UDA, H
    CHEMISTRY LETTERS, 1977, (12) : 1491 - 1494
  • [48] Studies towards the synthesis of the Amphomycin antibiotics: Total synthesis of Laspartomycin
    Binder, Randall J.
    VanNieuwenhze, Michael S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [49] Model studies towards the synthesis of catharanthine.
    Zhang, HJ
    Lynch, SM
    Padwa, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 229 : U369 - U369
  • [50] Studies towards the total synthesis of diazonamide A.
    Davies, JR
    Moody, CJ
    Kane, PD
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U147 - U147