TANDEM 1,3-DIPOLAR CYCLOADDITION AND ELECTROPHILIC CYCLIZATION REACTIONS - CYCLIC ETHER SUBUNITS OF POLYETHER ANTIBIOTICS FROM UNSATURATED ISOXAZOLINES

被引：36
|
作者：
KURTH, MJ
RODRIGUEZ, MJ
OLMSTEAD, MM
机构：
[1] Department of Chemistry, University of California
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 01期
关键词：
D O I：
10.1021/jo00288a047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new strategy for the construction of polyether antibiotic substructural units [spiroketals (I), tetrahydrofurans (II), and tetrahydropyrans (III)] consisting of bis-addition of an oxygen nucleophile across an a,co-diene moiety (i.e., IV) is described. The method exploits a tandem 1,3-dipolar cycloaddition/electrophilic cyclization sequence that proceeds via the intermediacy of an isoxazoline. Experiments presented illustrate the versatility of this strategy, which provides a unique exploit of the control elements operative in dipolar cycloaddition and electrophilic cyclization chemistry. © 1990, American Chemical Society. All rights reserved.
引用
收藏
页码：283 / 288
页数：6
相关论文
共 50 条
  • [31] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF VINYLCEPHALOSPORINS WITH DIAZOALKANES
    PITLIK, J
    GUNDA, TE
    MISKOLCZI, I
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1990, 27 (05) : 1281 - 1285
  • [32] 1,3-Dipolar cycloaddition of a cyclic nitrone derived from 2-deoxy-D-ribose to α,β-unsaturated lactones: An entry to carbapenem antibiotics
    Pieczykolan, Michal
    Staszewska-Krajewska, Olga
    Furman, Bartlomiej
    Chmielewski, Marek
    CARBOHYDRATE RESEARCH, 2016, 433 : 89 - 96
  • [33] Modeling the 1,3-dipolar cycloaddition of nitrones to vinylboranes in competition with boration, cyclization, and oxidation reactions
    Rastelli, A
    Gandolfi, R
    Sarzi-Amadé, M
    Carboni, B
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07): : 2449 - 2458
  • [34] Synthesis of iminosugars via 1,3-dipolar cycloaddition reactions of nitrones to α,β-unsaturated sugar aldonolactones
    Stecko, Sebastian
    Jurczak, Margarita
    Panfil, Irma
    Furman, Bartlomiej
    Grzeszczyk, Barbara
    Chmielewski, Marek
    COMPTES RENDUS CHIMIE, 2011, 14 (01) : 102 - 125
  • [35] REACTIVITY OF UNSATURATED ORGANOPHOSPHORUS COMPOUNDS IN 1,3-DIPOLAR CYCLOADDITION OF DIARYLDIAZOMETHANES
    PUDOVIK, AN
    GAREEV, RD
    STABROVS.LA
    EVSTAFEV, GI
    REMIZOV, AB
    ZHURNAL OBSHCHEI KHIMII, 1973, 43 (08): : 1674 - 1682
  • [36] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF ALKENYLALKOXYCARBENE CHROMIUM COMPLEXES
    BALDOLI, C
    DELBUTTERO, P
    LICANDRO, E
    MAIORANA, S
    PAPAGNI, A
    ZANOTTIGEROSA, A
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 476 (02) : C27 - C29
  • [37] CORNERSTONE WORKS FOR CATALYTIC 1,3-DIPOLAR CYCLOADDITION REACTIONS
    Kanemasa, Shuji
    HETEROCYCLES, 2010, 82 (01) : 87 - 200
  • [38] A DFT study of 1,3-dipolar cycloaddition reactions of 5-membered cyclic nitrones with α,β-unsaturated lactones and with cyclic vinyl ethers:: Part 1
    Stecko, Sebastian
    Pasniczek, Konrad
    Michel, Carine
    Milet, Anne
    Perez, Serge
    Chmielewski, Marek
    TETRAHEDRON-ASYMMETRY, 2008, 19 (14) : 1660 - 1669
  • [39] 1,3-dipolar cycloaddition reactions of porphyrins with azomethine ylides
    Silva, AMG
    Tomé, AC
    Neves, MGPMS
    Silva, AMS
    Cavaleiro, JAS
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (06): : 2306 - 2314
  • [40] 1,3-Dipolar cycloaddition reactions of azomethine ylides and alkynes
    Anna V. Gulevskaya
    Julia I. Nelina-Nemtseva
    Chemistry of Heterocyclic Compounds, 2018, 54 : 1084 - 1107
12345