While L-sugars are promising candidates in medicinal chemistry, such as L-ribose-containing nucleosides, only their D-forms naturally occur, thus prompting the need for an efficient synthetic methodology.
In this aim, Gaik-Khuan Chuah et al. at the National University of Singapore have devised a novel route to access rare L-lyxose and L-ribose in a simple 5-step procedure, leading to significantly increased yields and greener conditions as compared to previous reports.
To overcome the critical step for the oxidation of D-sugar to the corresponding D-lactone, the authors have used a heterogeneous catalyst – palladium-bismuth supported on carbon – and molecular oxygen, thus eliminating the need for bromine often used for this oxidation. The catalyst can easily be separated from the reaction mixture and reused, which enhances even further the relevance of this novel protocol.
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Reference
A heterogeneous Pd–Bi/C catalyst in the synthesis of L-lyxose and L-ribose from naturally occurring D-sugars
Ao Fan, Stephan Jaenicke and Gaik-Khuan Chuah
Org. Biomol. Chem., 2011, Advance Article
DOI: 10.1039/C1OB06116J, Paper
