Spiropentane mimics of nucleosides: Analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological …

…, JC Drach, ER Kern, J Zemlicka

Index: Guan, Hui-Ping; Ksebati, Mohamad B.; Cheng, Yung-Chi; Drach, John C.; Kern, Earl R.; Zemlicka, Jiri Journal of Organic Chemistry, 2000 , vol. 65, # 5 p. 1280 - 1290

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Citation Number: 45

Abstract

Synthesis of spirocyclic analogues of 2'-deoxyadenosine and 2'-deoxyguanosine (12a-15a and 12b-15b) is described. Rhodium-catalyzed reaction of ethyl diazoacetate with methylenecyclopropane 19, obtained from 2-bromo-2-bromomethylcyclopropane 17 via debromination (16), reduction (18), and acetylation (19), gave a mixture of all four isomeric spiropentanes 20a-20d. Hydrolysis afforded hydroxy carboxylic acids 21a-21d. ...

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