AN UNUSUALLY FACILE [3,3]-SIGMATROPIC REARRANGEMENT IN A STEREOSPECIFIC SYNTHESIS OF NOVEL 2',3'-DIDEOXYNUCLEOSIDE PRECURSORS

被引：14
|
作者：
ARMSTRONG, PL
COULL, IC
HEWSON, AT
SLATER, MJ
机构：
[1] SHEFFIELD HALLAM UNIV, DIV CHEM, SHEFFIELD S1 1WB, S YORKSHIRE, ENGLAND
[2] SHEFFIELD HALLAM UNIV, HLTH RES INST, SHEFFIELD S1 1WB, S YORKSHIRE, ENGLAND
[3] WELLCOME RES LABS, BECKENHAM BR3 3BS, KENT, ENGLAND
来源：
TETRAHEDRON LETTERS | 1995年 / 36卷 / 24期
关键词：
D O I：
10.1016/0040-4039(95)00747-Z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The glycal 5 is converted to intermediates which undergo, under mild conditions, thermal aza-Claisen rearrangements, leading to the amides 7 and 8 and the 2-pyrimidone 9, all potential precursors to 2',3'-dideoxynucleosides.
引用
收藏
页码：4311 / 4314
页数：4
相关论文
共 50 条
  • [41] STEREOSPECIFIC SYNTHESIS OF (+/-)-(E)-NUCIFEROL VIA [2,3]-SIGMATROPIC REARRANGEMENT OF ALLYLIC SULFOXIDES
    GRIECO, PA
    FINKELHO.RS
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12): : 2245 - 2247
  • [42] DIENOL-BENZENE REARRANGEMENT OF PROPARGYLCYCLOHEXADIENOLS - AROMATIC (1,2)-SIGMATROPIC, (3,3)-SIGMATROPIC AND (3,4)-SIGMATROPIC REARRANGEMENTS
    HEIMGARTNER, H
    SCHMID, H
    ZSINDELY, J
    HANSEN, HJ
    HELVETICA CHIMICA ACTA, 1972, 55 (04) : 1113 - +
  • [43] Enantiomeric synthesis of 2′,3′-dideoxy-3′-fluoro-L-apio nucleosides using [3,3]•sigmatropic rearrangement
    Choi, YS
    Lee, K
    Hong, JH
    Chu, CK
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U454 - U454
  • [44] SYNTHESIS OF 2'(AND-3')-METHYLENE-2'(AND-3')-DEOXYNUCLEOSIDES AND FACILE [3,3]-SIGMATROPIC REARRANGEMENT OF THEIR 5'-O-SILYL-3'(AND-2')-O-PHENOXYTHIOCARBONYL DERIVATIVES
    SAMANO, V
    ROBINS, MJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1990, 200 : 326 - ORGN
  • [45] Stereospecific Access to α- and β-N-Glycosylamine Derivatives by a Metal Free O-to-N [3,3]-Sigmatropic Rearrangement
    Pratesi, Debora
    Mirabella, Stefania
    Petrucci, Giulia
    Matassini, Camilla
    Faggi, Cristina
    Cardona, Francesca
    Goti, Andrea
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (38)
  • [46] Synthesis of novel 2′,3′-didehydro-2′,3′-dideoxynucleoside
    Yadava, VS
    ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (04) : 2857 - 2859
  • [47] Efficient synthesis of indoles using [3,3]-sigmatropic rearrangement of N-trifluoroacetyl enehydrazines
    Miyata, O
    Takeda, N
    Kimura, Y
    Takemoto, Y
    Tohnai, N
    Miyata, M
    Naito, T
    TETRAHEDRON, 2006, 62 (15) : 3629 - 3647
  • [48] THERMALLY INDUCED [3,3] SIGMATROPIC REARRANGEMENT OF N-ALLYLHYDRAZONES
    STEVENS, RV
    MCENTIRE, EE
    BARNETT, WE
    WENKERT, E
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (18) : 662 - 663
  • [49] SYNTHESIS OF STRAINED 8-MEMBERED HETEROCYCLIC ALLENES BY [3,3] SIGMATROPIC REARRANGEMENT AND THEIR REACTIVITIES
    HARUSAWA, S
    MORIYAMA, H
    OHISHI, H
    YONEDA, R
    KURIHARA, T
    HETEROCYCLES, 1994, 38 (09) : 1975 - 1978
  • [50] INFLUENCE OF THE SUBSTITUENT IN A THIOPHENE RING ON [3,3]-SIGMATROPIC THE REARRANGEMENT OF ALLYLTHIENYLSULFIDES
    ANISIMOV, AV
    PANOV, SM
    VIKTOROVA, YA
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1982, (09): : 1195 - 1197
12345