1375950-93-8Relevant academic research and scientific papers
Total synthesis of the myxobacterial macrolide ripostatin b?
Glaus, Florian,Altmann, Karl-Heinz
, p. 227 - 230 (2013/07/25)
This 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. Schweizerische Chemische Gesellschaft.
Total synthesis of RNA-polymerase inhibitor ripostatin B and 15-deoxyripostatin A
Tang, Wufeng,Prusov, Evgeny V.
, p. 3401 - 3404 (2012/06/29)
Keep me skipped: A highly convergent total synthesis of ripostatin B, an inhibitor of the bacterial RNA polymerase, is described. The key steps to construct and avoid isomerization of the skipped triene are a double Stille cross-coupling reaction and a ring-closing metathesis. Furthermore, 15-deoxyripostatin A, a stable and conformationally locked analogue of ripostatin A (see scheme, 15-OH group red), was prepared and tested in vivo. Copyright
Total synthesis of the bacterial RNA polymerase inhibitor ripostatin B
Glaus, Florian,Altmann, Karl-Heinz
, p. 3405 - 3409 (2012/06/29)
A modular and highly stereoselective synthesis of the title compound was developed. Key steps in the assembly of the carbon framework of ripostatin B (1; see scheme) were a stereoselective Paterson aldol reaction and a high-yielding ring-closing metathesis mediated by Grubbs first generation catalyst. The C15 hydroxy group was established through Tishchenko-Evans reduction in excellent yield and selectivity. Copyright
