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Following a new strategy, an improved total synthesis of the unique antibiotic octacidomycin (1) and of structurally related oligocarboxylic acids was developed (Scheme 1,2). Starting from 3 and the tetraethylester of 1,17-dibromo-6,6,12,12-heptadecane-tetracarboxylic acid (6 ) as a key compound, systematical fragment condensations lead to the nonatriacontanepentadecacarboxylic acid 11 and hence to the 1,3,9,15,21,27,33,39-nonatriacontane-octacarboxylic acid 1. The synthetic pathway can easily be modified and generally be applied for the synthesis of a broad variety of hitherto unknown oligocarboxylic acids or their esters, respectively, and even of cyclic analogues (Scheme 2).

zeitschrift für naturforschung b

Octacidomycine, IV : Neue Totalsynthese von rac-Octacidomycin und strukturverwandten Oligocarbonsäuren / Octacidomycins, IV : A New Total Synthesis of rac-Octacidomycin and Structurally Related Oligocarboxylic Acids