Synthesis 2017; 49(04): 770-774
DOI: 10.1055/s-0036-1588324
paper
© Georg Thieme Verlag Stuttgart · New York

4,5-Disubstituted 1-Methylimidazoles via Cyclization of Defined α-Aminoketones: Synthesis of Fungerin and Analogues I

Daniel Przybyla
Institut für Organische Chemie/Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz, Germany   Email: nubbemey@uni-mainz.de
,
Udo Nubbemeyer*
Institut für Organische Chemie/Johannes Gutenberg-Universität Mainz, Duesbergweg 10–14, 55128 Mainz, Germany   Email: nubbemey@uni-mainz.de
› Author Affiliations
Further Information

Publication History

Received: 20 July 2016

Accepted after revision: 06 September 2016

Publication Date:
23 September 2016 (online)


Abstract

A protocol for the chemoselective synthesis of the fungal metabolite fungerin has been developed. First the required N-methyl α-aminoketone was generated starting from sarcosine, propiolic acid, and prenyl bromide. Marckwald thioimidazole cyclization and subsequent sulfur removal delivered the target fungerin as well as an analogue, respectively, displaying defined substitution patterns.

Supporting Information

 
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