AMINO ACID ANALOGS OF BENANOMICIN A THROUGH DESALANINEBENANOMICIN A

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Desalaninebenanomicin A has been synthesized in good yield by the cleavage of the amido bond of benanomicin A using MEERWEIN'S reagent. This is a useful intermediate to prepare amino acid analogs of benanomicin A. MEERWEIN'S reagent reacts with totally protected benanomicin A to give a stable imino ether. After deprotection, the imino ether is treated with aqueous acetone at reflux to afford a methyl ester of desalaninebenanomicin A. Desalaninebenanomicin A was coupled with a variety of amino acids by the active ester method to afford new benanomicin analogs.