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Tuscolid and Tuscoron A and B: Isolation, Structural Elucidation and Studies on the Biosynthesis of Novel Furan‐3(2 H )‐one‐Containing Metabolites from the Myxobacterium Sorangium Cellulosum
Author(s) -
Niggemann Jutta,
Herrmann Martina,
Gerth Klaus,
Irschik Herbert,
Reichenbach Hans,
Höfle Gerhard
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300539
Subject(s) - chemistry , stereochemistry , tetrahydropyran , dihydropyran , ring (chemistry) , biosynthesis , polyketide , furan , derivative (finance) , enzyme , catalysis , organic chemistry , financial economics , economics
Three 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 13 C‐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(2 H )‐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 1 H‐ 1 H‐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)