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- W2791496642 abstract "Described is the total synthesis of the myxobacterial natural product ripostatin B and of a small number of analogs. Ripostatin B is a polyketide-derived 14-membered macrolide that acts as an inhibitor of bacterial RNA-polymerase, but is mechanistically distinct from rifamycin-derived RNA-polymerase inhibitors that are in use for tuberculosis treatment. The macrolactone ring of ripostatin B features two stereocenters and a synthetically challenging doubly skipped triene motif, with one of the double bonds being in conjugation with the ester carbonyl. Appended to the macrolactone core are an extended hydroxy-bearing phenylalkyl side chain at C13 and a carboxymethyl group at C3. The triene motif was established with high efficiency by ring-closing olefin metathesis, which proceeded in almost 80% yield. The side chain-bearing stereocenter α to the ester oxygen was formed in a Paterson aldol reaction between a methyl ketone and a β-chiral β-hydroxy aldehyde with excellent syn selectivity (dr >10:1). The total synthesis provided a blueprint for the synthesis of analogs with modifications in the C3 and C13 side chains. The C3-modified analogs showed good antibacterial activity against efflux-deficient Escherichia coli but, as ripostatin B, were inactive against Mycobacterium tuberculosis, in spite of significant in vitro inhibition of M. tuberculosis RNA-polymerase." @default.
- W2791496642 created "2018-03-29" @default.
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- W2791496642 date "2018-03-15" @default.
- W2791496642 modified "2023-10-12" @default.
- W2791496642 title "Total Synthesis of Ripostatin B and Structure–Activity Relationship Studies on Ripostatin Analogs" @default.
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- W2791496642 cites W1969128991 @default.
- W2791496642 cites W1970862953 @default.
- W2791496642 cites W1972295774 @default.
- W2791496642 cites W1973191530 @default.
- W2791496642 cites W1973714359 @default.
- W2791496642 cites W1978974567 @default.
- W2791496642 cites W1982168502 @default.
- W2791496642 cites W1982183474 @default.
- W2791496642 cites W1982796443 @default.
- W2791496642 cites W1984566317 @default.
- W2791496642 cites W2002592515 @default.
- W2791496642 cites W2003120439 @default.
- W2791496642 cites W2003150036 @default.
- W2791496642 cites W2005477338 @default.
- W2791496642 cites W2005654754 @default.
- W2791496642 cites W2010732799 @default.
- W2791496642 cites W2012475762 @default.
- W2791496642 cites W2018616596 @default.
- W2791496642 cites W2022412731 @default.
- W2791496642 cites W2027709497 @default.
- W2791496642 cites W2029978813 @default.
- W2791496642 cites W2035983545 @default.
- W2791496642 cites W2036317207 @default.
- W2791496642 cites W2044324168 @default.
- W2791496642 cites W2047112403 @default.
- W2791496642 cites W2048543473 @default.
- W2791496642 cites W2057752347 @default.
- W2791496642 cites W2058623521 @default.
- W2791496642 cites W2068230294 @default.
- W2791496642 cites W2070105304 @default.
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- W2791496642 cites W2074652739 @default.
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- W2791496642 cites W2085519327 @default.
- W2791496642 cites W2089997464 @default.
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- W2791496642 cites W2098494808 @default.
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- W2791496642 cites W2320382374 @default.
- W2791496642 cites W2323943045 @default.
- W2791496642 cites W2324823558 @default.
- W2791496642 cites W2343223522 @default.
- W2791496642 cites W29080555 @default.
- W2791496642 cites W2946096662 @default.
- W2791496642 cites W2949728005 @default.
- W2791496642 cites W2949843463 @default.
- W2791496642 cites W2950007866 @default.
- W2791496642 cites W2950648249 @default.
- W2791496642 cites W2951309910 @default.
- W2791496642 cites W2951542685 @default.
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- W2791496642 doi "https://doi.org/10.1021/acs.joc.8b00193" @default.
- W2791496642 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/29542926" @default.
- W2791496642 hasPublicationYear "2018" @default.
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