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Next, the reaction mixture was stirred at room temperature for a further 24h. Then, the reaction mixture was concentrated under reduced pressure to give a yellow oil. Purification on silica gel using the CombiFlash system (EtOAc\/CHCl3 0\u219250%) gave the pure product of the reaction 7 as colorless oil. After 3-times repeated evaporation with n-pentane the oil was transformed to white amorphous solid. Yield: 893 mg, 80%. Isolated as a white amorphous solid, >95% pure by NMR and a single spot by TLC; Rf: 0.63 in 50% EtOAc\/CHCl3, strains green with PMA; 1H NMR (403 MHz, CD2Cl2) \u03b4 7.05 (dd, J = 6.8, 6.0 Hz, 1H), 6.12 (dd, J = 10.7, 2.2 Hz, 1H), 5.97 (dd, J = 10.7, 1.6 Hz, 1H), 4.47 (dddd, J = 19.4, 15.2, 9.7, 7.8 Hz, 1H), 4.21\u20134.07 (m, 2H), 4.04\u20133.99 (m, 1H), 3.98\u20133.91 (m, 1H), 3.86 (d, J = 7.5 Hz, 1H), 3.80 (q, J = 6.8 Hz, 1H), 3.75 (dd, J = 10.1, 2.5 Hz, 1H), 3.68 (dd, J = 9.9, 2.5 Hz, 1H), 3.63 (dd, J = 11.0, 3.2 Hz, 1H), 2.98 (dq, J = 9.4, 7.3 Hz, 1H), 2.71\u20132.63 (m, 1H), 2.53 (dt, J = 8.5, 2.7 Hz, 1H), 2.44 (s, 1H), 2.40 (d, J = 8.5 Hz, 1H), 2.33 (dt, J = 12.6, 10.1 Hz, 1H), 2.18 (ddd, J = 12.5, 9.8, 2.7 Hz, 1H), 1.95 (ddd, J = 12.5, 8.9, 2.6 Hz, 1H), 1.91\u20130.82 (m, 45H), 0.77 (d, J = 7.0 Hz, 3H), 0.72 (d, J = 6.7 Hz, 3H) ppm; 13C NMR (101 MHz, CD2Cl2) \u03b4 213.5, 176.4, 134.1, 126.7, 124.0, 120.4, 106.8, 99.1, 89.2, 80.2, 77.3, 75.9, 74.8, 71.2, 70.9, 69.5, 67.3, 53.6, 48.6, 46.8, 40.8, 40.4, 40.1, 39.8, 38.6, 37.3, 36.6, 32.9, 31.0, 30.4, 29.5, 28.6, 27.1, 26.0, 22.3, 22.2, 20.7, 17.9, 17.3, 15.8, 15.0, 14.7, 14.4, 11.7, 11.5, 8.6, 6.5. One signal overlapping; 19F NMR (379 MHz, CD2Cl2) \u03b4 \u201373.01, \u201373.04, \u201373.07 ppm; FT-IR (KBr tablet): 3502 (br, s), 3454 (br, s), 3365 (br, s), 2970 (s), 2937 (s), 2877 (s), 1713 (s), 1689 (s), 1678 (s), 1530 (s), 1459 (s), 1386 (s) cm\u22121; ESI MS (m\/z): [M+Na]+ Calcd for C44H72F3NNaO10 855; Found 855. The ESI MS, 1H, 13C and 19F NMR spectra of 7 are included in the Supplementary material (Figs. S2\u2013S5)."},{"key":"10.1016\/j.bmcl.2020.127062_b0110","unstructured":"Synthesis of 2,2,2-trifluoroethyl amide of C20-oxosalinomycin (8): To a stirred solution of 2,2,2-trifluoroethyl amide of salinomycin (7) (500 mg, 0.60 mmol, 1.0 equiv.) in CH2Cl2 at room temperature, activated manganese(IV) oxide (1040 mg, 11.96 mmol, 20.0 equiv.) was added in one portion. The resulting black suspension was stirred vigorously for 3 days, and then filtrated over Celite. The filtrate was concentrated under reduced pressure to give a colorless oil. Purification on silica gel using the CombiFlash system (EtOAc\/n-hexane 0\u219233%) gave the pure product of the reaction 8 as colorless oil. After 3-times repeated evaporation with n-pentane the oil was transformed to white amorphous solid. Yield: 396 mg, 79%. Isolated as a white amorphous solid, >95% pure by NMR and a single spot by TLC; Rf: 0.71 in 50% EtOAc\/n-hexane. UV-active and strains green with PMA; 1H NMR (400 MHz, CDCl3) \u03b4 7.30 (d, J = 10.8 Hz, 1H), 7.25 (dd, J = 6.6, 5.2 Hz, 1H), 6.25 (d, J = 10.7 Hz, 1H), 4.51\u20134.29 (m, 2H), 4.06\u20133.97 (m, 2H), 3.89 (dddd, J = 19.5, 15.0, 9.9, 5.2 Hz, 2H), 3.81\u20133.76 (m, 1H), 3.73 (dd, J = 10.0, 2.8 Hz, 1H), 3.68 (dd, J = 9.9, 2.2 Hz, 1H), 3.51 (s, J = 17.3 Hz, 1H), 3.35 (dd, J = 10.9, 2.0 Hz, 1H), 2.95 (d, J = 5.9 Hz, 1H), 2.87\u20132.81 (m, 1H), 2.81\u20132.74 (m, 1H), 2.66\u20132.54 (m, 2H), 2.05 (ddd, J = 16.2, 8.9, 4.9 Hz, 1H), 1.97\u20130.83 (m, 44H), 0.76 (d, J = 6.8 Hz, 3H), 0.65 (d, J = 7.0 Hz, 3H) ppm; 13C NMR (101 MHz, CDCl3) \u03b4 213.9, 189.6, 175.8, 142.8, 128.2, 126.1, 123.3, 105.8, 97.3, 89.7, 79.3, 77.6, 75.2, 72.8, 71.1, 70.8, 69.9, 53.5, 48.1, 46.1, 40.5, 40.1, 39.8, 39.7, 39.5, 38.2, 36.1, 34.7, 33.6, 32.5, 30.4, 29.0, 28.2, 26.6, 24.6, 22.2, 20.6, 20.2, 17.4, 17.3, 15.8, 14.5, 14.3, 13.6, 11.31, 11.30, 7.8, 6.6 ppm; 19F NMR (283 MHz, CDCl3) \u03b4 \u201372.60, \u201372.63, \u201372.67 ppm; FT-IR (KBr tablet): 3467 (br, s), 3331 (br, s), 2972 (s), 2937 (s), 2878 (s), 1705 (s), 1673 (s), 1535 (s), 1460 (s), 1384 (s) cm\u20131; ESI MS (m\/z): [M+Na]+ Calcd for C44H70F3NNaO10 853; Found 853. The ESI MS, 1H, 13C and 19F NMR spectra of 8 are included in the Supplementary material (Figs. S6\u2013S9)."},{"key":"10.1016\/j.bmcl.2020.127062_b0115","unstructured":"The studies of antimicrobial activity were conducted using a series of reference strains of bacteria from international microbe collections, i.e. American Type Culture Collection (ATTC) and National Collection of Type Culture (NCTC). Among reference strains used there were 8 Gram(+) bacteria (Staphylococcus aureus NCTC 4163, ATCC 29213, 25923 and 6538; Staphylococcus epidermidis ATCC 12228 and 35984; Enterococcus hirae ATCC 10541; and Micrococcus luteus ATCC 9341) as well as 4 Gram(\u2013) bacteria (Pseudomonas aeruginosa ATCC 15442 and 27853; and Escherichia coli NCTC 8196 and ATCC 25922)."},{"key":"10.1016\/j.bmcl.2020.127062_b0120","unstructured":"The antimicrobial activity was expressed by the values of minimum inhibitory concentration (MIC), according to CLSI reference procedures with some modification. MIC was tested by the two-fold serial microdilution method (in 96-well microtiter plates) on Mueller-Hinton broth. The final inoculum of all studied bacteria was 106 CFU mL\u20131 (colony forming unit per mL). The stock solution of tested compounds was prepared in DMSO, and diluted in sterile medium to maximum 1% of solvent content. The tested concentrations of compounds were from 0.25 to 256 \u00b5g mL\u22121. The MIC was defined after 18h of incubation at 35 \u00b0C, and it was found as a value of the lowest compound concentration which inhibited the visible growth of tested strains37."},{"key":"10.1016\/j.bmcl.2020.127062_b0125","doi-asserted-by":"crossref","first-page":"995","DOI":"10.1016\/j.bbamem.2015.01.005","volume":"1848","author":"Antonenko","year":"2015","journal-title":"Biochim Biophys Acta Biomembr"},{"key":"10.1016\/j.bmcl.2020.127062_b0130","doi-asserted-by":"crossref","first-page":"2108","DOI":"10.1016\/j.bbamem.2012.04.017","volume":"1818","author":"Huczy\u0144ski","year":"2012","journal-title":"Biochim Biophys Acta Biomembr"},{"key":"10.1016\/j.bmcl.2020.127062_b0135","doi-asserted-by":"crossref","unstructured":"Antoszczak M, Rutkowski J, Huczy\u0144ski A. In Bioactive Natural Products. Chemistry and Biology; Brahmachari G., Ed.; Wiley-VCH: Weinheim, 2015; 1st Edition, chapter 6, pp. 107\u2013170.","DOI":"10.1002\/9783527684403.ch6"},{"key":"10.1016\/j.bmcl.2020.127062_b0140","doi-asserted-by":"crossref","first-page":"57","DOI":"10.3184\/003685002783238870","volume":"85","author":"Stapleton","year":"2002","journal-title":"Sci Prog"},{"key":"10.1016\/j.bmcl.2020.127062_b0145","doi-asserted-by":"crossref","DOI":"10.1371\/annotation\/f1a4d192-57b9-43fb-a248-379e0f5a46ca","volume":"8","author":"Du","year":"2013","journal-title":"PLoS ONE"},{"key":"10.1016\/j.bmcl.2020.127062_b0150","doi-asserted-by":"crossref","first-page":"496","DOI":"10.1086\/647350","volume":"17","author":"Pittet","year":"1996","journal-title":"Infect Control Hosp Epidemiol"},{"key":"10.1016\/j.bmcl.2020.127062_b0155","unstructured":"The antibiofilm activity assay (crystal violet) was performed based on O\u2019Toole protocol with some minor modifications.38 Tested cultures of Staphylococcus epidermidis (ATCC 12228, ATCC 35984, MR 654, and MR 660) and Staphylococcus aureus (MR 583, and MR 584) strains were visualized for biofilm formation by staining with 0.1% crystal violet (CV) aqueous solution, and measuring the absorbance at OD595. An overnight culture (180 r min\u22121 at 37 \u00b0C) was centrifuged and diluted in fresh TSB medium reached 0.1 at 600 nm at an optical density, and used for further cultivation of flat-bottomed microtiter plate (a total of 100 \u03bcL bacteria suspension per well). 100 \u03bcL of each diluted compounds were transferred into bacteria suspension, and plates were then incubated for 24h at 37 \u00b0C. Bacteria suspensions (5x105 colony-forming unit per mL) without compound were used as controls. The cell turbidity was monitored using a microtiter plate reader at OD600. After an incubation period, the medium was removed from wells and biofilm was three times washed with PBS. The wells were then stained with 0.1% CV and incubated at room temperature for 20\u2009min after staining was complete; CV in the wells was pulled out and the wells were washed with distilled water. The dye bound to the bacteria biomass was resolubilized by addition into wells a 30% (v\/v) glacial acetic acid and the plates were incubated at room temperature for 20 min at the shaker platform. The solutions from each well were transferred to a new microtiter plate, and the absorbance was measured at 595 nm using 30% acetic acid as a blank. All tests were carried out in triplicates and the results were averaged."},{"key":"10.1016\/j.bmcl.2020.127062_b0160","doi-asserted-by":"crossref","DOI":"10.1101\/cshperspect.a010306","volume":"3","author":"Kostakioti","year":"2013","journal-title":"Cold Spring Harb Perspect Med"},{"key":"10.1016\/j.bmcl.2020.127062_b0165","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1016\/j.jcma.2017.07.012","volume":"81","author":"Jamal","year":"2018","journal-title":"Chin Med Assoc"},{"key":"10.1016\/j.bmcl.2020.127062_b0170","doi-asserted-by":"crossref","first-page":"183","DOI":"10.3389\/fmicb.2014.00183","volume":"5","author":"Charlebois","year":"2014","journal-title":"Front Microbiol"},{"key":"10.1016\/j.bmcl.2020.127062_b0175","unstructured":"The DNA-damaging activity was tested by rec-assay, using two genetically modified Bacillus subtilis strains, i.e. M45 (rec\u2013) and H17 (rec+)[36,39]. Bacillus subtilis M45 is devoid of the recombinant-based DNA repair mechanism and is much more susceptible to DNA toxic substances compared to Bacillus subtilis H17 strain. The Bacillus subtilis strains were an effective microbial system for identification of potentially genotoxic compounds causing DNA damage susceptible to postreplicational repair[36]. The Bacillus subtilis rec-assay was performed according to the method of Kada with some minor modifications.39 Tested compounds were dissolved in DMSO and 10 \u00b5L of each solution was dripped onto sterile filter paper discs (Whatman no. 3) to load 256 \u00b5g of a given compound per 9 mm disc. Discs were placed on the surface of Nutrient agar plates (Difco, Poland) inoculated with 100 \u00b5L of bacterial culture (overnight), and incubated at 35 \u00b0C for 24h. After incubation, the growth inhibition zones (GIZ) were measured. NOQ (4-nitroquinoline N-oxide) was used as the reference genotoxin in concentration 2 \u00b5g per disc. Results of the genotoxicity test were read after 24h of incubation at 35 \u00b0C by comparing the diameter of the inhibition zone for the Bacillus subtilis M45 (rec\u2013) strain with that observed for the Bacillus subtilis H17 (rec+) strain. The result was interpreted as positive if zone of growth inhibition of highly sensitive rec\u2013 strain appeared 5 mm or longer than this of wild-type rec+ strain."},{"key":"10.1016\/j.bmcl.2020.127062_b0180","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1128\/jb.125.2.489-500.1976","volume":"125","author":"Sadaie","year":"1976","journal-title":"J Bacteriol"},{"key":"10.1016\/j.bmcl.2020.127062_b0185","unstructured":"Clinical and Laboratory Standards Institute, Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard M07-A11. Wayne, P. A., 2018."},{"key":"10.1016\/j.bmcl.2020.127062_b0190","first-page":"2437","volume":"47","author":"O\u2019Toole","year":"2011","journal-title":"J Vis Exp"},{"key":"10.1016\/j.bmcl.2020.127062_b0195","doi-asserted-by":"crossref","unstructured":"Kada T. 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