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. 2012 Jan 16;55(4):1706–1720. doi: 10.1021/jm201571p

Scheme 1. Synthesis of 4″-Dephospho-adenophostin A (4).

Scheme 1

Reagents and conditions: (a) BnBr, NaH, DMF, 0 °C–room temperature, 2 h. (b) 80% aqueous HOAc, reflux, 1 h. (c) Bu2SnO, BnBr, Bu4NBr, MeCN, 3 Å molecular sieves, reflux, 24 h. (d) Bu4NHSO4, BnBr, DCM: 5% aqueous NaOH (1:1), room temperature. (e) Ac2O, pyr, room temperature, 12 h. (f) Compound 16, NIS, TMSOTf, dioxane:toluene (3:1 v/v), 3 Å molecular sieves, room temperature, 30 min. (g) 90% TFA, room temperature, 15 min. (h) Ac2O, pyr, room temperature, 3 h. (i) 6-Chloropurine, BSA, TMSOTf, MeCN, 70 °C, overnight. (j) NH3, EtOH, 70 °C, 5 days. (k) (1) (BnO)2PN(iPr)2, ImOTf, DCM, room temperature, 30 min; (2) mCPBA, −78 °C–room temperature, 1 h. (l) Cyclohexene, Pd(OH)2, MeOH, H2O, 80 °C, overnight.