The partial synthesis of 54 derivatives of thiangazole A (1a), with modifications in the styryl region is the aldehyde 27, obtained by direct cleavage of the C-21/C-22 double bond. a new polythiazoline antibiotic from Polyangium spec. (myxobacteria), is described. Derivatives with chemical 27 was transformed into the oximes 37-42 and by Wittig reaction to (21Z)-thiangazole (43) and analogues 44-46 with modification of the carboxamide group in the oxazole region were prepared either by N-alkylation to amides 5-14 or by proton and alkyl residues replacing phenyl. 21,22-Didehydrothiangazole (50) was synthesized in a multi-step methanolysis to ester 15, and its transformation products 16, 19, 20. Oxidation of the C-5 methyl group of 1a with reaction from 27 via the 20-alkinyl intermediate 49. The insecticidal activities and inhibition of the respiratory chain molecular oxygen led to the hydroxymethyl derivative 21, and two by-products lacking the C-5 methyl group (22), or (complex I) by the thiangazole analogues were determined and compared with the natural product. the entire oxazole ring (23). Key intermediate for analogues Present address: Dragoco Gerberding & Co. AG D-37601 Holzminden.
sonЈs reagent [12] in toluene at 120°C furnished the Supporting information for this article is available on the thionoamide 4 in yield of 82%. For the synthesis of the WWW under http://www.wiley-vch.de/home/eurjoc or from the author. amides 8Ϫ14 (lacking the original N-methyl group), 1a was