Synthesis of saramycetic acid

The first reported synthesis of saramycetic acid, a degradation product of the complex thiopeptide antibiotic cyclothiazomycin, is achieved in nine steps and 11% overall yield from diethoxyacetonitrile by a strategy, which incorporates two Hantzsch thiazole syntheses using thioamides prepared from the corresponding nitriles without the use of gaseous H2S. The synthetic material was transformed to methyl saramycetate, which had spectroscopic properties in excellent agreement with the literature data.

The synthesis of saramycetic acid is reported from 2,2-diethoxyacetonitrile in nine steps and 11% overall yield. It incorporates 'gaseous H2S-free' nitrile thionations and Hantzsch thiazole syntheses to give synthetic material that was readily elaborated to methyl saramycetate with spectroscopic properties in agreement with the literature data.