257278-58-3Relevant articles and documents
Chemical modification of thiangazole A in the oxazole and styryl region
Herrmann, Martina,Ehrler, Juerg,Kayser, Hartmut,Rindlisbacher, Alfred,Hoefle, Gerhard
, p. 3381 - 3392 (2007/10/03)
The partial synthesis of 54 derivatives of thiangazole A (1a), a new polythiazoline antibiotic from Polyangium spec. (myxobacteria), is described. Derivatives with chemical modification of the carboxamide group in the oxazole region were prepared either by N-alkylation to amides 5-14 or by methanolysis to ester 15, and its transformation products 16, 19, 20. Oxidation of the C-5 methyl group of 1a with molecular oxygen led to the hydroxymethyl derivative 21, and two by-products lacking the C-5 methyl group (22), or the entire oxazole ring (23). Key intermediate for analogues with modifications in the styryl region is the aldehyde 27, obtained by direct cleavage of the C-21/C-22 double bond. 27 was transformed into the oximes 37- 42 and by Wittig reaction to (21Z)-thiangazole (43) and analogues 44-46 with proton and alkyl residues replacing phenyl. 21,22-Didehydrothiangazo1e (50) was synthesized in a multi-step reaction from 27 via the 20-alkinyl intermediate 49. The insecticidal activities and inhibition of the respiratory chain (complex I) by the thiangazole analogues were determined and compared with the natural product.
