A s y m m e t r i c S y n t h e s i s o f 4 ¢ -e p i -T r a c h y c l a d i n e s A a n d BAbstract: The first asymmetric synthesis of 4¢-epi-trachycladines A and B is reported. Starting from 2,2-dimethyl-1,3-dioxan-5-one the title nucleosides were synthesised in 14 steps employing the SAMP-/RAMP-hydrazone methodology. The dioxanone-SAMPhydrazone was first transformed into a trisubstituted derivative by a triple a-/a¢-alkylation. Removal of the chiral auxiliary and subsequent reduction gave the corresponding alcohol, which could be transformed over four steps into TBS-protected 2¢-C-methyl-5¢-deoxy-L-lyxose. The trachycladines were then obtained via the corresponding triacetate using standard Vorbrüggen and silyl-HilbertJohnson conditions in an overall yield of 18-21%. Such 2¢-Cbranched ribonucleosides are potential agonists for adenosine receptors and play an important role in drug discovery.
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