Model synthesis of six-membered carbocyclic spironucleosides

0351445 - ÚOCHB 2011 RIV CZ eng J - Journal Article
Nencka, Radim - Hřebabecký, Hubert - Dračínský, Martin
Model synthesis of six-membered carbocyclic spironucleosides.
Collection of Czechoslovak Chemical Communications. Roč. 75, č. 12 (2010), s. 1259-1272. ISSN 0010-0765
R&D Projects: GA MŠMT 1M0508
Institutional research plan: CEZ:AV0Z40550506
Keywords : spironucleosides * carbocyclic * Bucherer-Bergs reaction * Michaels addition * tandem reaction
Subject RIV: CC - Organic Chemistry
Impact factor: 0.853, year: 2010

Model study focusing on the synthesis of carbocyclic spironucleosides is presented. Hydantoin base was built on the easily accessible ketone precursors by Bucherer–Bergs reaction. On saturated substrates the reaction proceeded smoothly. On α,β-unsaturated ketones, however, the Bucherer–Bergs reaction competed with Michael addition of cyanide ion. We showed that the equilibrium of the reaction could be significantly shifted depending on the applied reaction conditions. Significant diastereoselectivity was observed for tandem Michael addition/Bucherer–Bergs reaction.
Permanent Link: http://hdl.handle.net/11104/0191199