Events The 8th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-8-01955

This submission belongs to the session a. General Organic Synthesis of the event The 8th International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Nov, 2004

Citation

M. Martinková, J. Gonda, M. Džoganová, A New Stereocontrolled Approach to a Key Intermediate in the Synthesis of (2S,3R)-capreomycidine, in Proceedings of The 8th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2004, MDPI: Basel, Switzerland, 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 ¹

J. Gonda ¹

M. Džoganová ¹

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.

Keywords

n/a

Contribution to the Stereoselective Synthesis of (3'S)-Isothiocyanato-3'-C-vinyl-3'-deoxyuridine and Its Derivatives

Oxidative Iodination of Aromatic Amines and Other Arenes, with Sodium Percarbonate as the Oxidant