Abstract
AbstractThree novel metabolites, tuscolid (1) and tuscoron A (2) and B (3), were isolated from the myxobacterium Sorangium cellulosum (strains So ce1401 and So ce1383). The structures were elucidated by detailed NMR spectroscopic analysis, and their biosynthesis was studied by feeding 13C‐labelled precursors. The results revealed that the macrolide 1 and the acyclic derivative 2 are closely related polyketides containing, as a characteristic structural feature, a furan‐3(2H)‐one ring system. The related minor component tuscoron B (3) was identified as an unstable structural analogue of tuscoron A. The relative stereochemistry of the tetrahydropyran ring and of C‐13 to C‐17 of tuscolid (1), and of the dihydropyran ring of tuscoron A (2), was determined on the basis of 1H‐1H‐coupling constants and NOE correlations. A tentative mechanism for the conversion of 1 into 2 is discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
Published Version
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