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. Author manuscript; available in PMC: 2020 Dec 17.
Published in final edited form as: J Med Chem. 2015 Feb 11;58(4):1915–1928. doi: 10.1021/jm501799k

Scheme 4.

Scheme 4.

Synthetic Route to Pyrrolyl DKAs 6k,l and 7k,la

aReagents and conditions: (i) NIS, acetone, −78 °C, 96 h; (ii) phenylboronic acid, Cs2CO3, P(t-But)3, Pd2(dba)3, dioxane, 80 °C, 24 h; (iii) diethyl oxalate, C2H5ONa, THF, room temp, 2 h; (iv) 1-trityl-1H-[1,2,4]triazole-3-carboxylic acid ethyl ester,36 n-BuLi, THF, from −78 to 0 °C, 3.5 h; (v) 3 M HCl sol, 1,4-dioxane, 60 °C, 30 min; (vi) 1 N NaOH, THF/CH3OH, room temp, 1 h.