Chondrochloren A and B, new β-amino styrenes from Chondromyces crocatus (myxobacteria)

In a screening for biologically active metabolites of the genus Chondromyces, two novel metabolites, chondrochloren A (1) and B (2), were isolated from several strains of C. crocatus. Compounds 1 and 2 are unique chloro-hydroxy-styryl amides of a highly modified C-14 carboxylic acid, which comprises an unsaturated ketone, two hydroxy, two methoxy and three methyl groups. After assignment of the absolute configuration of both carbinol stereocenters by Mosher's method, NMR spectroscopic data combined with MM2 calculations allowed the prediction of the preferred conformation in solution. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).