Efficient synthesis of 9- and 13-oxo leucomycin derivatives using hypervalent iodine reagents in solution and on solid support.

Zöllner T, Gebhardt P, Beckert R, Hertweck C (2005) Efficient synthesis of 9- and 13-oxo leucomycin derivatives using hypervalent iodine reagents in solution and on solid support. J Nat Prod 68(1), 112-114. PubMed

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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Identifier

PMID: 15679331