120712-73-4Relevant academic research and scientific papers
The Synthesis of Octacidomycin
Kerber, Karl-Heinz,Lackner, Helmut
, p. 719 - 726 (2007/10/02)
The total synthesis of octacidomycin (1), a novel oligocarboxylic acid antibiotic, and some shorter new model acids (19, 21, 24) is described.Key compounds in a series of fragment condensations of C19-, C5- and C2-units are α,α'-bis(bromopentyl)-substituted azealic- (6) and 3-(benzyloxypropyl)malonic esters (7).A six step synthesis yields bacteriostatically active octacidomycin (14=1). 14 and its octamethyl ester 15 are identical with the native products in all chemical and spectroscopic properties.Further combinations of fragments give tri-, tetra-, and pentacarboxylic acids.These demonstrate the flexibility of this widely variable synthetic method leading to new carboxylic acids and hydrocarbons.
