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

M. Martinková; J. Gonda; M. Džoganová

doi:10.3390/ecsoc-8-01955

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

M. Martinková

^*,

J. Gonda

M. Džoganová

¹ Department of Organic Chemistry, Institute of Chemistry, P. J. Šafárik University, SK-041 67 Košice, Slovakia

Published: 01 November 2004 by MDPI in The 8th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-8-01955

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.

Keywords: n/a

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M. Martinková

J. Gonda

M. Džoganová