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. Author manuscript; available in PMC: 2015 Nov 13.
Published in final edited form as: J Med Chem. 2013 Aug 2;56(16):6434–6456. doi: 10.1021/jm400652r

Scheme 2. Modifications to the acyl-chain.

Scheme 2

(a) HCl, MeOH. (b) BH3-Me2S, Anhydrous THF, 0 °C. (c) EDCI, DMAP, NH3 in dioxane (0.5M), THF. (d) EDCI, DMAP, (E)-4-methoxy-4-oxobut-2-enoic acid. (e) Anhydrous THF, (E)-methyl 4-chloro-4-oxobut-2-enoate, 4Å molecular sieves, 165 °C, µW. (f) methyl 4-oxobutanoate, BH3-Me2S, THF. (g) EDCI, DMAP, 4-fluorobutanoic acid, DCM (h) NaOH, EtOH:H2O.