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Enantioselective Synthesis of Ferrocenyl Nucleoside Analogues with Apoptosis-Inducing Activity
journal contribution
posted on 2006-06-22, 00:00 authored by Philippe James, Jörg Neudörfl, Moritz Eissmann, Patrick Jesse, Aram Prokop, Hans-Günther SchmalzAs a contribution to bioorganometallic chemistry, an enantioselective synthesis of novel carbocyclic nucleoside analogues with a ferroceno-cyclopentene backbone was developed. Diastereoselective cuprate 1,4-addition or Mukaiyama−Michael addition to a planar-chiral enoate (ethyl
(E)-2-[2-methoxycarbonyl-ferrocenyl]-acrylate) allowed for the introduction of different side chains (RCH2). Other important steps include a
Dieckmann cyclization and the attachment of the nucleobase (NB) in an iron-assisted SN1 reaction. Some of the target compounds were
shown to exhibit significant apoptosis-inducing activity (LD50 = 10−20 μM) against tumor cells.
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exhibitattachmentbioorganometallic chemistryside chainsRCHActivityAethylnucleobaseNBcuprateenantioselective synthesisFerrocenyl Nucleoside AnaloguesSNnovel carbocyclic nucleoside analoguesDieckmann cyclizationLD 50tumor cellsDiastereoselectiveEnantioselective SynthesisMukaiyamaenoateintroductiontarget compoundscontribution
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