Skip to main content
. Author manuscript; available in PMC: 2022 Apr 5.
Published in final edited form as: Eur J Med Chem. 2021 Feb 6;215:113272. doi: 10.1016/j.ejmech.2021.113272

Scheme 1.

Scheme 1.

Synthesis of cyclopentane-based MraY inhibitors 10 (JH-MR-21) and 11 (JH-MR-22).a

a Reagents and conditions: (a) Pd/C, H2, MeOH, 25 °C, 5 h; (b) Boc2O, DMAP, MeCN, 25 °C, 1 h, 81% for two steps; (c) NaBH4, MeOH, 25 °C, 3 h, 80%; (d) H2O, reflux, 20 h, 80%; (e) 3-ethoxyacryloyl isocyanate, 4 Å MS, DMF, −20 to 25 °C, 15 h, 49%; (f) 1 N H2SO4, reflux, 30 min, 68%; (g) IBX, MeCN, 80 °C, 1.5 h; (h) Ph3P=CHCO2t-Bu, THF, 0 °C, 12 h, 45% for two steps; (i) CbzNH2, K2OsO2(OH)4, (DHQD)2AQN, t-BuOCl, n-PrOH, 0.6 N NaOH, 5 to 25 °C, 2 h, 46% (dr >20:1); (j) 8, NIS, TESOTf, CH2Cl2, 4 Å MS, 25 °C, 30 min, 53%; (k) PPh3, THF/toluene (1/1), H2O, 25 °C, 12 h, 63%; (l) 80% TFA in THF/H2O (1/1), 25 °C, 14 h; For 10: 41%; For 11: 91%.