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. Author manuscript; available in PMC: 2018 May 11.
Published in final edited form as: J Med Chem. 2017 Apr 19;60(9):3958–3978. doi: 10.1021/acs.jmedchem.7b00259

Scheme 8.

Scheme 8

aReagents and conditions: (a) i. Ti(OEt)4, THF, reflux, ii. NaBH4, THF, -48 °C; (b) i. HCI/MeOH, ether, r.t., ii. Boc2O, Et3N, MeOH/THF, r.t.; (c) NaH, THF, °C - r.t., then Mel, 0°C - r.t.; (d) K4Fe(CN)6 × 3 H2O, t-BuXPhos G3, t-BuXPhos, 1:1 KOAc in H2O: dioxane, 100 °C; (e) i. [lr(OCH3)(COD)]2, dtbpy, Pin2B2, hexanes, 50 °C, ii. Oxone, H2O/acetone, 0 °C-r.t.; (e) i. NaH, DMF, 0 °C; ii. 44 (in DMF), 0 °C-50 °C; (f) i. K2CO3, MeOH, reflux, ii, HCI/MeOH, ether, r.t.