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Publicly Available Published by De Gruyter April 27, 2012

Synthesis of myxobacteria metabolites

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

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.


Conference

International Symposium on the Chemistry of Natural Products and the 7th International Conference on Biodiversity (ISCNP-27 & ICOB-7), International Conference on Biodiversity, International Symposium on the Chemistry of Natural Products, ICOB, ISCNP, Biodiversity, Natural Products, 27th, Brisbane, Australia, 2011-07-10–2011-07-15


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Online erschienen: 2012-4-27
Erschienen im Druck: 2012-4-27

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