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. 2016 Apr 26;2(5):351–358. doi: 10.1021/acscentsci.6b00057

Figure 2.

Figure 2

Synthesis of the cyclophellitol aziridine inhibitors 1, 2, probes 3–6 and 1,6-epi-cyclophellitol 7. Reagents and conditions: (a) (i) Li, NH3, THF, −60 °C, 57%; (ii) PhCH(OMe)2, CSA, DMF, 61%. (b) CCl3CN, DBU, DCM, 0 °C. (c) NaHCO3, I2, H2O, two step yield 41%. (d) 37% HCl aq, dioxane. (e) NaHCO3, MeOH, two step yield 63%. (f) 1-Azido-8-iodooctane, K2CO3, DMF, 80 °C, 39%. (g) 13, 14, 15, or 16, CuSO4, sodium ascorbate, DMF, 38% 3, 11% 4, 24% 5, 23% 6. (h) mCPBA, DCM, 40 °C, 44%. (i) Pd(OH)2/C, H2, MeOH, 68%.