Figure - PMC

Skip to main content

View full-text article in PMC

. Author manuscript; available in PMC: 2015 Dec 2.

Published in final edited form as: Bioorg Med Chem. 2014 Jan 23;22(5):1726–1735. doi: 10.1016/j.bmc.2014.01.017

Scheme 5 — Reagents and conditions: (i) LiAlH₄, THF, 0 °C, 2 h, 58%; (ii) PhCH(OEt)₂, CSA, CH₂Cl₂, reflux, 24 h, 85%; (iii) TsCl, Et₃N, CH₂Cl₂, 16 h, 83%; (iv) NaN₃, DMF, reflux, 16 h, 93%; (v) H₂, Pd/C, MeOH, 2 h, 75%; (vi) 4-nitrophenyl chlorosulfate, CH₂Cl₂, −78 °C, 2 h, 50%; (vii) 27, Et₃N, CH₂Cl₂, 4 Å molecular sieves; (viii) 4:1 TFA–H₂O, −35 °C, 4 h, 4% from 26.