An expeditious synthesis of the ascomycete metabolite rigidiusculamide B?

Organic & Biomolecular Chemistry Pub Date: 2016-09-12 DOI: 10.1039/C6OB01836J

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.

Graphical abstract: An expeditious synthesis of the ascomycete metabolite rigidiusculamide B
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