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. Author manuscript; available in PMC: 2022 Jul 22.
Published in final edited form as: J Med Chem. 2021 Jul 12;64(14):9960–9988. doi: 10.1021/acs.jmedchem.1c00184

Scheme 1:

Scheme 1:

Synthesis of compounds (±)-6a-fa

aReagents and conditions: a) Appropriate aryl aldehyde, Cs2CO3, 1,4- dioxane, 110 °C, 14 h, 40–100%; b) phenylhydrazine, H2SO4, 1,4-dioxane, 70 °C, 2 h then 25 °C, 14 h, 30–66%; c) NaBH4, MeOH, 25 °C, 12 h or H2/Pd, MeOH, 25 °C, 12 h, 40–100%; d) methyl 4-formylbenzoate, NaBH3CN, EtOH, AcOH, 70 °C, 14 h, 25–43%; e) NH2OH (50% in H2O), KOH, DCM/MeOH from 0 °C to 25 °C, 12 h, 33–73%.