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

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.

Key words

imidazole - α-aminoketone - Marckwald synthesis - regioselective synthesis - natural product

• References


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