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Spiropentane mimics of nucleosides: analogues of 2'-deoxyadenosine and 2'-deoxyguanosine. Synthesis of all stereoisomers, isomeric assignment, and biological activity.
Guan HP, Ksebati MB, Cheng YC, Drach JC, Kern ER, Zemlicka J. Guan HP, et al. J Org Chem. 2000 Mar 10;65(5):1280-90. doi: 10.1021/jo991030r. J Org Chem. 2000. PMID: 10814087
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 h …
Rhodium-catalyzed reaction of ethyl diazoacetate with methylenecyclopropane 19, obtained from 2-bromo-2-bromomethylcyclopropane 17 via debro …