An enantioselective synthesis of the C3-C21 segment of the macrolide immunosuppressive agent FR252921

被引：7
|
作者：
Ghosh, Arun K. [1 ]
Rodriguez, Samuel
机构：
[1] Purdue Univ, Dept Chem, 560 Oval Dr, W Lafayette, IN 47907 USA
来源：
TETRAHEDRON LETTERS | 2016年 / 57卷 / 26期
基金：
美国国家卫生研究院;
关键词：
FR252921; Macrolide; Synthesis; Immunosuppressive; Asymmetric; Aldol reaction; Asymmetric reduction; FLUORESCENS NO. 408813; PROMISING IMMUNOSUPPRESSANT; CYCLOSPORINE-A; ACID-B; REDUCTION; INHIBITOR; KETONES; ROUTE;
D O I：
10.1016/j.tetlet.2016.05.067
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An enantioselective synthesis of the C3-C21 segment of the novel immunosuppressant FR252921 is described. The C12 and C13 stereogenic centers were constructed by a non-aldol process utilizing optically active 4-phenylbutyrolactone. The C18 stereogenic center was installed using Braun's highly diastereoselective acetate aldol reaction. Other key steps involved Curtius rearrangement and Horner-Wadsworth-Emmons olefination reactions. (C) 2016 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2884 / 2887
页数：4
相关论文
共 50 条
  • [31] ASYMMETRIC-SYNTHESIS OF THE C(17)-C(27) SEGMENT OF THE ANTINEOPLASTIC MACROLIDE BRYOSTATIN-1
    HALE, KJ
    LENNON, JA
    MANAVIAZAR, S
    JAVAID, MH
    HOBBS, CJ
    TETRAHEDRON LETTERS, 1995, 36 (08) : 1359 - 1362
  • [32] Toward a synthesis of the antitumor macrolide peloruside A: a chiral pool approach for the C(1)-C(11) segment
    Gurjar, MK
    Pedduri, Y
    Ramana, CV
    Puranik, VG
    Gonnade, RG
    TETRAHEDRON LETTERS, 2004, 45 (02) : 387 - 390
  • [33] Synthetic studies of antitumor macrolide laulimalide:: a stereoselective synthesis of the C17-C28 segment
    Ghosh, AK
    Wang, Y
    TETRAHEDRON LETTERS, 2000, 41 (24) : 4705 - 4708
  • [34] A flexible route to immunosuppressive agent FR252921.: Asymmetric total synthesis of its (13R,14R,19R)-isomer
    Yu, Shouyun
    Liu, Feng
    Ma, Dawei
    TETRAHEDRON LETTERS, 2006, 47 (51) : 9155 - 9157
  • [35] Synthesis of the enantiopure C21-C26 segment of apoptolidin.
    Chen, YZ
    Fuchs, PL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U217 - U217
  • [36] Synthesis of the C21-C28 segment of pectenotoxin-4
    Kolakowski, Robert V.
    Williams, Lawrence J.
    TETRAHEDRON LETTERS, 2007, 48 (27) : 4761 - 4764
  • [37] Synthesis of the C1-C8 tetrahydropyranyl segment of the antifungal agent ambruticin and its C3 epimer
    Liu, LP
    Donaldson, WA
    SYNLETT, 1996, (01) : 103 - 104
  • [38] Enantioselective synthesis of the C-14 to C-5 cyclopentane segment of jatrophane diterpenes
    Helmboldt, H
    Rehbein, J
    Hiersemann, M
    TETRAHEDRON LETTERS, 2004, 45 (02) : 289 - 292
  • [39] Enantioselective synthesis of the C11-C24 segment of macrolactin A via organoiron methodology
    Prahlad, V
    Donaldson, WA
    TETRAHEDRON LETTERS, 1996, 37 (51) : 9169 - 9172
  • [40] ENANTIOSPECIFIC SYNTHESIS OF THE C-17-C-20 AND C-21-C-27 SYNTHONS OF THE ANTINEOPLASTIC MACROLIDE BRYOSTATINS
    ROY, R
    REY, AW
    CHARRON, M
    MOLINO, R
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (18) : 1308 - 1310
12345