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. Author manuscript; available in PMC: 2018 Feb 15.
Published in final edited form as: Eur J Med Chem. 2016 Oct 27;127:793–809. doi: 10.1016/j.ejmech.2016.10.059

Scheme 6. Synthesis of Homoserinol construct 52.

Scheme 6

Reagents and conditions a) 9-deazaadenine, CH2O, EtOH, 60 °C, 52% b) H2, Pd(OH)2–C, 93% c) FmocCl, NaHCO3, MeOH, then BzCl, pyridine then THF – AcOH, 2:1 then DMTrCl, pyridine, 35%. d) 5, tetrazole, CH2Cl2 then 19, tetrazole, CH2Cl2 then, t-BuOOH, 58% e) HCl-MeOH, 61% f) 17, tetrazole, CH2Cl2 then t-BuOOH, 19% then H2, Pd – C then NH4OH, 50 °C, 19%.