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. Author manuscript; available in PMC: 2020 May 31.
Published in final edited form as: J Med Chem. 2020 Mar 17;63(6):3298–3316. doi: 10.1021/acs.jmedchem.9b02078

Scheme 1.

Scheme 1.

General Synthetic Route to PVHIsa

a Conditions and reagents (General Procedures are detailed in Experimental Section): GP1, N,O-dimethylhydroxylamine hydrochloride, T3P, DIPEA, DCM, and 0 °C; GP2, LAH, THF, and −10 °C; GP3, (1) NaBH4, EtOH, and 0 °C and (2) SOCl2 and DCM; GP4, PPh3, benzene, and reflux; GP5, P(OEt)3 and 150 °C; GP6, LHMDS, THF, −70 to 0 °C; GP7, LHMDS, THF, −70 to 0 °C; GP8, (1) TFA, DCM, and 0 °C and (2) R1-Xaa-OH, T3P, DIPEA, DCM, and 0 °C; GP9, MeI, MeCN, and reflux; GP10, (1) LiOH and H2O and (2)ClCOOEt and NH4Cl.