A New Stereocontrolled Approach to a Key Intermediate in the Synthesis of (2S,3R)-Capreomycidine
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 diastereomerically (4R,5R)-4- vinyltetrahydro-1H-imidazole-2-thione derivative.