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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Efficient synthesis of 9- and 13-oxo leucomycin derivatives using hypervalent iodine reagents in solution and on
Tina Zöllner1, Peter Gebhardt, Rainer Beckert
1Hans-Knöll-Institute for Natural Products Research, Beutenbergstrasse 11a, 07745 Jena, Germany.
Abstract:
An efficient procedure for the highly selective oxidation of leucomycines to the corresponding 16-membered 9- and 13-oxo macrolides using hypervalent iodinates is presented. Both the Dess-Martin periodinane (DMP) and polymer-bound 2-iodoxybenzoic acid (IBX) show clear advantages over the previously employed manganese dioxide. Key intermediates for a variety of further chemical derivatization methods (2a, 2b) are obtained in very good yields without the requirement of protecting groups.
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