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. Author manuscript; available in PMC: 2015 Jan 9.
Published in final edited form as: J Med Chem. 2013 Dec 24;57(1):171–190. doi: 10.1021/jm401577c

Scheme 4.

Scheme 4

aReagents: (a) p-TsCl, pyr, 40 °C (91%); (b) i) K(s-Bu)3BH, THF, −78 °C; ii) NaOH, 30% H2O2 (71% overall); (c) MeMgBr, toluene, reflux (91%); (d) ClCH2OMe, (i-Pr)2EtN, CH2Cl2, 0 °C (90%); (e) O3, CH2Cl2, −78 °C; ii) Zn dust, AcOH (65% overall); (f) NaOH, MeOH/H2O (75%); (g) Li/liq. NH3, THF (72%); (h) 6 N HCl, MeOH (92%); (i) Ac2O, Et3N, DMAP (95%); (j) CrO3, AcOH, 60 °C; (k) AcCl, MeOH (51%, steps j & k); (l) NaOMe, THF, reflux (71%); (m) LiCl, DMF, 160 °C (86%).