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. Author manuscript; available in PMC: 2016 Aug 10.
Published in final edited form as: J Med Chem. 2016 Apr 4;59(7):3471–3488. doi: 10.1021/acs.jmedchem.6b00085

Scheme 4.

Scheme 4

aConditions: (a) SO2Cl2, 15 °C, AcOH:Et2O (9:1), 1 h; (b) NBS, AIBN, CCl4, 80 °C, 4 h; (c) NaN3, MeOH:H2O (10:1), 25 °C, 12 h; (d) PPh3, THF:H2O (10:1), 25 °C, 12 h; (e) LiOH, THF:MeOH:-H2O (9:1:1), 25 °C, 10 h; (f) LDA, MeI, THF, −40 °C, 3 h; (g) LiAlH4, THF, 0–25 °C, 12 h; (h) DBU, DPPA, toluene, 25 °C, 12 h; (i) n-BuLi, CO2(g), THF, −78 °C, 2 h.