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A New Stereocontrolled Approach to a Key Intermediate in the Synthesis of (2S,3R)-capreomycidine
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1  Department of Organic Chemistry, Institute of Chemistry, P. J. Šafárik University, SK-041 67 Košice, Slovakia

Abstract: A new synthetic approach to the key intermediate in the stereoselective synthesis of (2S,3R)-capreomycidine was developed. The synthesis is based on novel domino reaction combining (3,3)-sigmatropic rearrangement of chiral allylic thiocyanate derived from D-methionine and intramolecular amino addition to arising isothiocyanate to produce diastereommerically (4R,5R)-4-vinyltetrahydro-1H-imidazole-2-thione.
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