ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

A New Stereocontrolled Approach to a Key Intermediate in the Synthesis of (2S,3R)-Capreomycidine

M. Martinková, J. Gonda, and M. Džoganová

Department of Organic Chemistry, Institute of Chemistry, P. J. Šafárik University, SK-041 67 Košice

E-mail: mmartin@kosice.upjs.sk

Received: 23 March 2004

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 diastereomerically (4R,5R)-4- vinyltetrahydro-1H-imidazole-2-thione derivative.

Full paper in Portable Document Format: 584a292.pdf

Chemical Papers 58 (4) 292–293 (2004)