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. Author manuscript; available in PMC: 2020 Mar 30.
Published in final edited form as: ChemistrySelect. 2018 Nov 29;3(44):12625–12629. doi: 10.1002/slct.201802475

Scheme1. Synthesis of 5’-F-platensimycin 7b.

Scheme1.

Reagents and conditions: (a) K2CO3 (5 equiv.), BnOH (2.5 equiv.), DMF, 105 °C, 16 h, 85%; (b) 6 N KOH, EtOH, 140 °C, 1.5 h, 95%; (c) MeOH, DMAP (0.1 equiv.), EDCI (1.2 equiv.), NEt3 (2.5 equiv.), 10 h, 65%; (d) H2 (1.1 atm.), 10% Pd/C (0.2 equiv.), MeOH, 25 °C, 3 h, 90%; (e) 65% HNO3, CHCl3, 5 min, 72%; (f) 3 (1.0 equiv.), HATU (2.0 equiv.), NEt3 (3.0 equiv.), DCM, 25 °C, 12 h, 83%; (g) aq. KOH, MeOH, 45 °C, 4 h, 89%. Abbreviations: Bn = benzyl, DMF = N,N-dimethylformamide, DMAP = dimethylaminopyridine, EDCI = 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, HATU = 1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate, DCM = dichloromethane.