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The Journal of Organic Chemistry

Synthesis of chain-extended and C-6'functionalized precursors of the nucleoside antibiotic sinefungin

JW Lyga, JA Secrist III

文献索引:Lyga, John W.; Secrist, John A. Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 1982 - 1988

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被引用次数: 28

摘要

Employment of 2-oxo-3-(triphenylphosphoranylidene) tetrahydrofuran (7) gave a nucleoside lactone (8) which was converted in several steps to a C-6'carboxylic acid (1Oc). A Curtius rearrangement of this acid, quenching with benzyl alcohol, allowed the introduction of a C- 6'amino group, blocked as a urethane (lla). The chain-ending (C-8') alcohol was converted to a leaving group and displaced by azide ion and dibenzyl sodiomalonate.