Abstract
The ascomycete metabolite rigidiusculamide B was synthesised in six steps and 22% overall yield. The key steps were a Li2Te-triggered Dittmer-type Dieckmann cyclisation of an N-(α-haloacyl)tyrosine ester to give a 4-O-silyl tetramate, followed by its fluoride-assisted desilylation-oxidation with oxygen. The product 3-hydroxy-pyrrolidine-2,4-dione was obtained as a 6 : 1 mixture of separable diastereoisomers.
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