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Issue 39, 2016
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An expeditious synthesis of the ascomycete metabolite rigidiusculamide B

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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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Supplementary files

Article information


Submitted
22 Aug 2016
Accepted
06 Sep 2016
First published
12 Sep 2016

Org. Biomol. Chem., 2016,14, 9262-9266
Article type
Paper

An expeditious synthesis of the ascomycete metabolite rigidiusculamide B

A. Wunder and R. Schobert, Org. Biomol. Chem., 2016, 14, 9262
DOI: 10.1039/C6OB01836J

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