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. Author manuscript; available in PMC: 2011 Aug 2.

Published in final edited form as: J Med Chem. 2009 Aug 27;52(16):5228–5240. doi: 10.1021/jm900611t

Scheme 6 — Reagents and conditions: (a) KI, NaIO₄, conc. H₂SO₄, 25–30 ºC, 2 h; (b) (R)-(+)-1-(1-naphthyl)ethylamine 18, EDCI, HOBT, DIPEA, DMF/CH₂Cl₂ (1:1), 23 ºC, 48 h; (c) CuCN, KCN, DMF, 130 ºC, 16 h; (d) SOCl₂, MeOH, reflux, 4 h; (e) NBS, Bz₂O₂, CCl₄, reflux, 24 h; (f) NaH, NaOMe, MeOH, 50 ºC, 4 h; (g) LiOH·H₂O, THF/H₂O (5:1), 23 ºC, 1.5 h; (h) (R)-(+)-1-(1-naphthyl)ethylamine 18, EDCI, HOBT, DIPEA, DMF/CH₂Cl₂ (1:1), 23 ºC, 16 h; (i) H₂, Pd-C, EtOAc, 23 ºC, 10 h.