Total Synthesis of the Myxobacterial Macrolide Ripostatin B
Keywords:Antibiotics, Ring-closing metathesis, Ripostatin, Rna polymerase, Total synthesis
AbstractThis article describes the total synthesis of ripostatin B, which is a 14-membered macrolide of myxobacterial origin that inhibits E. coli RNA polymerase by a different mechanism of action than the first-line anti-tuberculosis drug rifampicin. Structurally, ripostatin B features a labile and synthetically challenging doubly skipped triene motif embedded in the macrolactone ring. Key steps in the synthesis were a Paterson aldol reaction, a low-temperature Yamaguchi esterification and an alkene metathesis reaction to close the macrolide ring. The natural product was synthesized in a longest linear sequence of 21 steps and 3.6% overall yield.
How to Cite
F. Glaus, K.-H. Altmann, Chimia 2013, 67, 227, DOI: 10.2533/chimia.2013.227.
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