Ring-rearrangement metathesis of substituted dihydropyrans and dihydrofurans

被引：12
作者：
Donnard, Morgan [1 ]
Tschamber, Theophile [1 ]
Le Nouen, Didier [1 ]
Desrat, Sandy [1 ]
Hinsinger, Karen [1 ]
Eustache, Jacques [1 ]
机构：
[1] Univ Haute Alsace, Ecole Natl Super Chim Mulhouse, CNRS, Lab Chim Organ & Bioorgan Associe, F-68093 Mulhouse, France
来源：
TETRAHEDRON | 2011年 / 67卷 / 02期
关键词：
Ring-rearrangement; Metathesis; Dihydropyrans; Dihydrofurans; CLOSING METATHESIS; OXIDATION; ALDEHYDES;
D O I：
10.1016/j.tet.2010.11.036
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The rearrangement of dihydropyrans and dihydrofurans featuring appending olefins has been studied. The rearranged products bear resemblance with polyunsaturated di- and trisaccharides. Examples of functionalization prior to, or following, rearrangement are provided suggesting that the method should be useful for the synthesis of nonclassical saccharides. This work also illustrates the power of cascade methatetic processes for increasing molecular complexity starting from relatively simple heterocycles. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：339 / 357
页数：19
相关论文
共 28 条
  • [1] De novo synthesis of oligosaccharides using a palladium-catalyzed glycosylation reaction
    Babu, RS
    Zhou, M
    O'Doherty, GA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (11) : 3428 - 3429
  • [2] New approaches to olefin cross-metathesis
    Blackwell, HE
    O'Leary, DJ
    Chatterjee, AK
    Washenfelder, RA
    Bussmann, DA
    Grubbs, RH
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) : 58 - 71
  • [3] DIRECT PREPARATION OF 2-DEOXY-D-GLUCOPYRANOSIDES FROM GLUCALS WITHOUT FERRIER REARRANGEMENT
    BOLITT, V
    MIOSKOWSKI, C
    LEE, SG
    FALCK, JR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (23) : 5812 - 5813
  • [4] A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS
    COREY, EJ
    WINTER, RAE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) : 2677 - &
  • [5] DENOOY AE, 1999, J ORG CHEM, V64, P293
  • [6] Stereoselective synthesis of 2,3-unsaturated 1,6-oligosaccharides by means of a glycal-derived allyl epoxide and N-nosyl aziridine
    Di Bussolo, Valeria
    Checchia, Lorenzo
    Romano, Maria Rosaria
    Pineschi, Mauro
    Crotti, Paolo
    [J]. ORGANIC LETTERS, 2008, 10 (12) : 2493 - 2496
  • [7] Ring-rearrangement metathesis of 3,6-dialkoxy-3,6-dihydro-2H-pyrans
    Donnard, Morgan
    Tschamber, Theophile
    Desrat, Sandy
    Hinsinger, Karen
    Eustache, Jacques
    [J]. TETRAHEDRON LETTERS, 2008, 49 (07) : 1192 - 1195
  • [8] Extended RCM-ROM sequences: a novel approach to polyunsaturated trisaccharides
    Donnard, Morgan
    Tschamber, Theophile
    Eustache, Jacques
    [J]. TETRAHEDRON LETTERS, 2008, 49 (51) : 7325 - 7327
  • [9] A MILD OXIDIZING REAGENT FOR ALCOHOLS AND 1,2-DIOLS - O-IODOXYBENZOIC ACID (IBX) IN DMSO
    FRIGERIO, M
    SANTAGOSTINO, M
    [J]. TETRAHEDRON LETTERS, 1994, 35 (43) : 8019 - 8022
  • [10] Study concerning the effects of chelation on the structure and catalytic activity of ruthenium carbene complexes
    Fürstner, A
    Thiel, OR
    Lehmann, CW
    [J]. ORGANOMETALLICS, 2002, 21 (02) : 331 - 335
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