Octacidomycins, IV: A new total synthesis of rac-octacidomycin and structurally related oligocarboxylic acids [German]

摘要

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). Starling 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 nonatriacontane-pentadecacarboxylic 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). [References: 8]