Synthesis of spiroacetal-nucleosides as privileged natural product-like scaffolds

被引:14
作者
Choi, Ka Wai [1 ]
Brimble, Margaret A. [1 ]
机构
[1] Univ Auckland, Dept Chem, Auckland, New Zealand
关键词
PROTEIN PHOSPHATASE INHIBITOR; (+)-SPIROLAXINE METHYL-ETHER; PYLORI AGENTS CJ-12,954; SPONGISTATIN; STEREOCONTROLLED SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; ABSOLUTE-CONFIGURATION; FACILE SYNTHESIS; BUILDING-BLOCKS; OKADAIC ACID;
D O I
10.1039/b818314g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The elaboration of a 6,6-spiroacetal scaffold to incorporate a nucleoside unit at the anomeric position is described. The novel spiroacetal-nucleoside hybrids 11 were generated via nucleosidation of cetoxy-spiroacetal 10 with a series of silylated nucleobases under Vorbruggen conditions.
引用
收藏
页码:1424 / 1436
页数:13
相关论文
共 77 条
  • [1] Synthesis of the bis-spiroacetal moiety of the polyether antibiotic CP44,161
    Allen, PR
    Brimble, MA
    Prabaharan, H
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (04): : 379 - 389
  • [2] Synthesis of 1,2,3-triazole and 1,2,3,4-tetrazole-fused glycosides and nucleosides by an intramolecular 1,3-dipolar cycloaddition reaction
    Anegundi, Ramakrishna I.
    Puranik, Vedavati G.
    Hotha, Srinivas
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (04) : 779 - 786
  • [3] [Anonymous], 2003, ANTIBIOTICS CHEMOTHE
  • [4] 2′-Spiro ribo- and arabinonucleosides:: synthesis, molecular modelling and incorporation into oligodeoxynucleotides
    Babu, BR
    Keinicke, L
    Petersen, M
    Nielsen, C
    Wengel, J
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (20) : 3514 - 3526
  • [5] 2',5'-BIS-O-(TERT-BUTYLDIMETHYLSILYL)-3'-SPIRO-5''-(4''-AMINO-1',2''-OXATHIOLE-2'',2''-DIOXIDE)PYRIMIDINE (TSAO) NUCLEOSIDE ANALOGS - HIGHLY SELECTIVE INHIBITORS OF HUMAN-IMMUNODEFICIENCY-VIRUS TYPE-1 THAT ARE TARGETED AT THE VIRAL REVERSE-TRANSCRIPTASE
    BALZARINI, J
    PEREZPEREZ, MJ
    SANFELIX, A
    SCHOLS, D
    PERNO, CF
    VANDAMME, AM
    CAMARASA, MJ
    DECLERCQ, E
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (10) : 4392 - 4396
  • [6] Bartoli G, 1998, SYNLETT, P209
  • [7] Natural product-guided synthesis of a spiroacetal collection reveals modulators of tubulin cytoskeleton integrity
    Barun, O
    Kumar, K
    Sommer, S
    Langerak, A
    Mayer, TU
    Müller, O
    Waldmann, H
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (22) : 4773 - 4788
  • [8] Toward improving the chemistry of N-acyliminium ions:: Nucleophilic substitution reactions of pyrrolidinone derivatives with trialkylsilyl nucleophiles catalyzed by triisopropylsilyltrifluoromethane sulfonate (TIPSOTf)
    Ben Othman, R
    Bousquet, T
    Fousse, A
    Othman, M
    Dalla, V
    [J]. ORGANIC LETTERS, 2005, 7 (14) : 2825 - 2828
  • [9] SPIROKETAL GLYCOMIMETICS - THE SYNTHESIS OF A CONFORMATIONALLY RESTRAINED SIALYL-LEWIS-X MIMIC
    BIRKBECK, AA
    LEY, SV
    PRODGER, JC
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (22) : 2637 - 2642
  • [10] WHY PENTOSE AND NOT HEXOSE NUCLEIC-ACIDS .2. PREPARATION OF OLIGONUCLEOTIDES CONTAINING 2',3'-DIDEOXY-BETA-D-GLUCOPYRANOSYL BUILDING-BLOCKS
    BOHRINGER, M
    ROTH, HJ
    HUNZIKER, J
    GOBEL, M
    KRISHNAN, R
    GIGER, A
    SCHWEIZER, B
    SCHREIBER, J
    LEUMANN, C
    ESCHENMOSER, A
    [J]. HELVETICA CHIMICA ACTA, 1992, 75 (05) : 1416 - 1477