Synthesis of chain-extended and C-6'functionalized precursors of the nucleoside antibiotic sinefungin
JW Lyga, JA Secrist III
Index: Lyga, John W.; Secrist, John A. Journal of Organic Chemistry, 1983 , vol. 48, # 12 p. 1982 - 1988
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Citation Number: 28
Abstract
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.
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