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

Scheme 2. Synthesis of 3″-Dephospho-adenophostin A (5).

Scheme 2

Reagents and conditions: (a) MeOH, NaOMe, room temperature, 30 min. (b) Dowex-H+. (c) PhCH(OMe)2, CSA, DMF, 70 °C. (d) BnBr, NaH, DMF, room temperature, 2 h. (e) TFA, Et3SiH, DCM, 0 °C. (f) Ac2O, pyr, room temperature, 3 h. (g) Compound 16, NIS, TMSOTf, dioxane:toluene, 3 Å molecular sieves, room temperature, 30 min. (h) 90% TFA, room temperature, 10 min. (i) 6-Chloropurine, BSA, TMSOTf, MeCN, 70 °C, overnight. (j) NH3, EtOH, 74 °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.