Efficient synthesis of 9- and 13-oxo leucomycin derivatives using hypervalent iodine reagents in solution and on solid support.
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.
Zöllner
Tina
T
Hans-Knöll-Institute for Natural Products Research, Beutenbergstrasse 11a, 07745 Jena, Germany.
Gebhardt
Peter
P
Beckert
Rainer
R
Hertweck
Christian
C
D002384:Catalysis; D007202:Indicators and Reagents; D007455:Iodine / Q000737:chemistry*; D015939:Kitasamycin / Q000031:analogs & derivatives / Q000032:analysis / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D007202:Indicators and Reagents; D015939:Kitasamycin; D007455:Iodine