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Pure Appl. Chem., 2012, Vol. 84, No. 6, pp. 1421-1433

Published online 2012-04-27

Synthesis of myxobacteria metabolites

Stephen L. Birkett, Darran A. Loits, Samantha Wimala and Mark A. Rizzacasa*

School of Chemistry, The Bio21 Institute, The University of Melbourne, Victoria 3010, Australia

Abstract: Myxobacteria are an excellent source of novel secondary metabolites with a range of biological activities. This review details the synthesis of several examples of these natural products. The total synthesis of all the members of the crocacin family is presented where the stereochemistry of the stereotetrad was set via a tin-mediated syn-aldol reaction followed by selective anti-reduction. The other key step in the route to crocacins A, B, and D was the introduction of the enamide functionality by acylation of an enecarbamate. A formal synthesis of apicularen A is also discussed, which involved a base-induced macrolactonization reaction and a transannular oxy-Michael cyclization to secure the tetrahydropyran ring. Finally, the total synthesis of deshydroxyajudazol B is summarized. This route details a modified approach to the 2,4-disubstituted oxazole, and a Diels–Alder reaction followed by aromatization was utilized to form the isochromanone moiety. A highly efficient Sonogashira coupling followed by partial reduction then gave deshydroxyajudazol B.