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. Author manuscript; available in PMC: 2022 Sep 26.
Published in final edited form as: Bioorg Med Chem Lett. 2020 Sep 12;30(24):127543. doi: 10.1016/j.bmcl.2020.127543

Scheme 5.

Scheme 5.

Synthesis of 38. Reagents and conditions: (a) OsO4, NMO, NaIO4, THF/H2O, rt, 1.5 h. (b) NaBH4, EtOH, rt, 3 h, 70–81%. (c) benzyl bromide, TBAF, rt, 6.5 h, 81–89%. (d) InCl3, ethyl diazoacetate, DCM, rt, 16 h, 57%. (e) LiOH, MeOH/H2O, rt, 3 h, 76–95%. (f) EDC•HCl, HOAt, 4-chloroaniline, DMF, rt, 16 h, 65–80%. (g) 10% Pd/C, H2 (1 atm), MeOH, rt, 1 h, 27–56%.