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. Author manuscript; available in PMC: 2019 Sep 13.
Published in final edited form as: J Med Chem. 2018 Aug 30;61(17):7877–7891. doi: 10.1021/acs.jmedchem.8b00827

Scheme 3. Synthesis of the VERU-111 Analogues 13a-fa.

Scheme 3.

aReagents and conditions: (a) SEMCl, NaH, THF, 0 °C to rt; (b) Pd2(dba)3, 2-dicydohexylphosphmo-2′,4′,6′-triisopropylbiphenyl, Na2CO3, toluene-MeOH-H2O (20:4:1), reflux; (c) benzoyl chlorides, i-PrMgCl(LiCl), THF, rt to reflux; (d) Pd(OAc)2, K2CO3, PPh3, n-BuOH, reflux; (e) TFA, DCM, rt.