Asymmetric synthesis of 4 '-quaternary 2 '-deoxy-3 '-epi-beta-C-nucleosides

An efficient diastereo- and enantioselective synthesis of 4'-quaternary 2'-deoxy-3'-epi-beta-C-nucleosides is described employing the RAMP-hydrazone methodology to establish the first stereocentre. Further key steps include diastereoselective nucleophilic 1,2-additions with Grignard a...

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Bibliographic Details
Published inSynlett no. 15; pp. 2391 - 2393
Main Authors Enders, D, Hieronymi, A, Ridder, A
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 19.09.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
diastereoselective reduction
asymmetric synthesis
ACID
DNA
NUCLEOSIDES
BIOLOGICAL-ACTIVITY
nucleoside analogues
organocerium reagents
CONFORMATION
hydrazones
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Summary:An efficient diastereo- and enantioselective synthesis of 4'-quaternary 2'-deoxy-3'-epi-beta-C-nucleosides is described employing the RAMP-hydrazone methodology to establish the first stereocentre. Further key steps include diastereoselective nucleophilic 1,2-additions with Grignard and organocerium reagents.
ISSN:0936-5214
DOI:10.1055/s-2005-872658