Synthetic studies on palmerolide C: synthesis of an advanced intermediate towards the revised structure of palmerolide C

被引：4
|
作者：
Sayyad, Ashik A. [1 ]
Kaim, Khushboo [1 ]
Kaliappan, Krishna P. [1 ]
机构：
[1] Indian Inst Technol, Dept Chem, Mumbai 400074, Maharashtra, India
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2020年 / 18卷 / 30期
关键词：
FORMAL TOTAL-SYNTHESIS; RING-CLOSING METATHESIS; MARINE NATURAL-PRODUCT; A SYNTHESIS; FRAGMENT; STRATEGY; ROUTE; DISCOVERY; MACROLIDE; CORE;
D O I：
10.1039/d0ob01140a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A stereoselective synthesis of the highly advanced intermediates towards the revised structure of palmerolide C and 10-epi-palmerolide C is described in this paper. The required key fragments C1-C6, C7-C14 and C15-C23 have been successfully assembled in a convergent manner to access the C1-C23 framework bearing all the five stereocenters present in the natural product. The synthesis involves the Julia-Kocienski reaction, Yamaguchi esterification, Takai olefination and regioselective epoxide opening as key steps. The proposed route is flexible and could also be applied to the synthesis of structurally related palmerolides.
引用
收藏
页码：5937 / 5950
页数：14
相关论文
共 50 条
  • [1] Studies towards the synthesis and structure determination of palmerolide C
    Wlochal, Joanna
    Eadie, Scott
    Florence, Gordon J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [2] Synthesis of the macrolactone core of the revised structure of palmerolide C
    Vaithegi, Kannan
    Pawar, Amit B.
    Prasad, Kavirayani R.
    TETRAHEDRON, 2021, 77
  • [3] Studies towards the synthesis of palmerolide A
    Eadie, Scott
    Murray, Ross
    Florence, Gordon J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [4] Synthesis of the Originally Proposed Structure of Palmerolide C
    Florence, Gordon J.
    Wlochal, Joanna
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (45) : 14250 - 14254
  • [5] Synthetic studies toward the total synthesis of palmerolide A
    Kaliappan, Krishna P.
    Pujari, Sandip A.
    Parthasarathy, Gowrisankar
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [6] Towards the synthesis of Palmerolide A: asymmetric synthesis of C1-C14 fragment
    Chandrasekhar, S.
    Vijeender, K.
    Chandrashekar, G.
    Reddy, Ch. Raji
    TETRAHEDRON-ASYMMETRY, 2007, 18 (20) : 2473 - 2478
  • [7] Synthetic studies towards the marine natural product palmerolide A: Synthesis of the C3-C15 and C16-C23 fragments
    Cantagrel, Guillaume
    Meyer, Christophe
    Cossy, Janine
    SYNLETT, 2007, (19) : 2983 - 2986
  • [8] Total synthesis of the originally proposed and revised structures of palmerolide A
    Nicolaou, K. C.
    Guduru, Ramakrishna
    Sun, Ya-Ping
    Banerji, Biswadip
    Chen, David Y. -K.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (31) : 5896 - 5900
  • [9] Synthetic studies on a marine natural product, palmerolide A: Synthesis of C1-C9 and C15-C21 fragments
    Kaliappan, Krishna P.
    Gowrisankar, Parthasarathy
    SYNLETT, 2007, (10) : 1537 - 1540
  • [10] Total synthesis of the originally proposed and revised structures of palmerolide A and isomers thereof
    Nicolaou, K.C.
    Sun, Ya-Ping
    Guduru, Ramakrishna
    Banerji, Biswadip
    Chen, David Y.-K.
    Journal of the American Chemical Society, 2008, 130 (11): : 3633 - 3644
12345