Enantioselective synthesis of the C5-C23 segment of biselyngbyaside

被引:13
|
作者
Chandrasekhar, Srivari [1 ]
Rajesh, Gontla [1 ]
Naresh, Tumma [1 ]
机构
[1] CSIR Indian Inst Chem Technol, Div Nat Product Chem, Hyderabad 500007, Andhra Pradesh, India
关键词
Biselyngbyaside; Julia-Kocienski olefination; Crimmin's acetate aldol reaction; STEREOSELECTIVE TOTAL-SYNTHESIS; ASYMMETRIC ALDOL ADDITIONS; BLUE-GREEN-ALGAE; ABSOLUTE-CONFIGURATIONS; NATURAL-PRODUCTS; CHEMICAL-SHIFTS; DIHYDROXYLATION; LAULIMALIDE; REAGENTS; FRAGMENT;
D O I
10.1016/j.tetlet.2012.11.015
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Stereo and enantioselective synthesis of C5-C23 fragment of cytotoxic marine natural product biselyngbyaside is achieved using E-selective methyl lithium addition onto enyne, Crimmin's acetate aldol reaction, Sharpless asymmetric epoxidation, and Julia-Kocienski olefination as the key steps. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:252 / 255
页数:4
相关论文
共 50 条
  • [41] An unusual reversal of stereoselectivity in a boron mediated aldol reaction:: Enantioselective synthesis of the C1-C6 segment of the epothilones
    Panicker, B
    Karle, JM
    Avery, MA
    TETRAHEDRON, 2000, 56 (40) : 7859 - 7868
  • [42] Enantioselective synthesis of the C1-C9 segment of bryostatin by kinetic resolution of racemic alpha-keto esters
    Kalesse, M
    Eh, M
    TETRAHEDRON LETTERS, 1996, 37 (11) : 1767 - 1770
  • [43] ENANTIOSELECTIVE SYNTHESIS OF THE C1,6-C21,16 SEGMENT OF MACBECIN-I AND MACBECIN-II
    BAKER, R
    CASTRO, JL
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (01): : 190 - 192
  • [44] Synthesis of the C1-C13 Segment of Poecillastrin C
    Clark, Hugh
    Hosokawa, Seijiro
    SYNLETT, 2024, 35 (13) : 1596 - 1600
  • [45] Enantioselective Total Synthesis of Aspergillide C
    Nagasawa, Tomohiro
    Kuwahara, Shigefumi
    ORGANIC LETTERS, 2009, 11 (03) : 761 - 764
  • [46] ENANTIOSELECTIVE SYNTHESIS OF A TAXOL C RING
    Ma, Cong
    Schiltz, Stephanie
    Prunet, Joelle
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2011, 76 (12) : 1579 - 1594
  • [47] Improved synthesis of the C8-C23 segment of aplysiatoxins via asymmetric dihydroxylation of the chiral homoallylic alcohol
    Toshima, H
    Ichihara, A
    BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (03) : 599 - 602
  • [48] ENANTIOSELECTIVE TOTAL SYNTHESIS OF (+)-BUCIDARASINS A AND C
    Usui, Kenji
    Nakada, Masahisa
    HETEROCYCLES, 2015, 91 (02) : 332 - 350
  • [49] Enantioselective Synthesis of Cephalimysins B and C
    Chalupa, David
    Vojackova, Petra
    Partl, Jiri
    Pavlovic, Drazen
    Necas, Marek
    Svenda, Jakub
    ORGANIC LETTERS, 2017, 19 (04) : 750 - 753
  • [50] Enantioselective Total Synthesis of (-)-Kibdelone C
    Butler, John R.
    Wang, Chao
    Bian, Jianwei
    Ready, Joseph M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (26) : 9956 - 9959