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. Author manuscript; available in PMC: 2014 Jan 4.
Published in final edited form as: J Med Chem. 2013 Jun 26;56(13):10.1021/jm400510u. doi: 10.1021/jm400510u

Scheme 1a.

Scheme 1a

aReagents and conditions: (a) isobutyric anhydride, cat. 4-(dimethylamino)pyridine (DMAP), Et3N, CH2Cl2, rt; (b) 10% Pd/C, H2, EtOAc/MeOH, rt; (c) 1-(tert-butoxycarbonyl)-(2S)-azetidinylmethanol, azodicarbonyldipiperidide (ADDP), P(n-Bu)3, PhMe, 0 °C to rt; (d) NaOMe, MeOH, 40 °C; (e) CF3COOH, CH2Cl2, rt; (f) i. (COCl)2, DMSO, Et3N, CH2Cl2, −78 °C; ii. Ph3P=CHCO2CH3, THF, 0 °C to rt; (g) LiAlH4, THF, rt; (h) 2N NaOH, MeOH/THF (1:1), rt; (i) i. NaH, CS2, DMF, 0 °C to rt; ii. MeI, rt; (j) 70% HF/pyridine, 1,3-dibromo-5,5-dimethylhydantoin (DBH), CH2Cl2, −78 °C; (k) I2, PPh3, imidazole, 0 °C to rt; (l) morpholine, piperidine, or piperazine, CH3CN; (m) NaN3, DMF, 60 °C; (n) 10% Pd/C, H2, ethanol, rt; (o) ethyl or isopropyl chloroformate, Et3N, 0 °C to rt.