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. Author manuscript; available in PMC: 2009 Dec 25.
Published in final edited form as: J Med Chem. 2008 Dec 25;51(24):7806–7819. doi: 10.1021/jm8008629

Scheme 2a.

Scheme 2a

a Reagents and conditions: (a) NaH, PhCH3, dimethyl carbonate, reflux; (b) 2 eq. LDA, THF, −78 °C; (c) bromopropionitrile; (d) LiCl, H2O, DMSO, reflux; (e) (CH2OH)2, TsOH, triethyl orthoformate, CH2Cl2; (f) Raney Ni, MeOH; (g) 6 M HCl, MeOH, reflux; (h) NaCNBH3, MeOH; (i) 13a/13b/13c, K2CO3, CH3CN, cat. KI, reflux; (j) LiAlH4, THF, reflux; (k) BBr3, CH2Cl2, −78 °C