Octacidomycine, IV: Neue Totalsynthese von rac-Octacidomycin und strukturverwandten Oligocarbonsäuren Octacidomycins, IV : A New Total Synthesis of rac-Octacidom ycin and Structurally Related Oligocarboxylic Acids
نویسنده
چکیده
A ndreas Krause, Helm ut Lackner* Institut für Organische Chemie der Universität Göttingen, Tammannstraße 2, D-37077 Göttingen Z. Naturforsch. 53 b, 1043-1050 (1998); eingegangen am 22. Juni 1998 Antibiotics, Octacidomycins, Oligocarboxylic Acids, Synthesis, NMR Data 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 l,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, respec tively, and even of cyclic analogues (Scheme 2).
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