Tetrahedron

A lithiation route to c-5 substitution of an imidazole nucleoside and its application to the synthesis of 3-deazaguanosine

H Tanaka, M Hirayama, M Suzuki, T Miyasaka…

Index: Tanaka; Hirayama; Suzuki; Miyasaka Tetrahedron, 1986 , vol. 42, # 7 p. 1971 - 1980

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Citation Number: 26

Abstract

Lithiation of a protected methyl 2-chloro-l-(β-D-ribofuranosyl) imidazole-4-carboxylate with LDA affords the C-5 anion which reacts with a wide range of electrophiles to provide various types of 5-substituted derivatives. Application of this method to the synthesis of 3- deazaguanosine, an antiviral nucleoside, is also described.