Reaction Steps
Methyl(2S)-2-(tert-butoxy)-2-[(22S)-5-ethenyl-16,17-difluoro-4,22,28-trimethyl-21,27-dioxa-1,7,34-triazahexacyclo[26.2.2.16,9.110,14.02,7.015,20]tetratriaconta-2,4,6(34),8,10(33),11,13,15(20),16,18-decaen-3-yl]acetate (0.15 g, 0.214 mmol, 1.0 equiv) was dissolved in dioxane (6.41 mL) and water (2.14 mL). To this solution was added sodium periodate (0.16 g, 0.748 mmol, 3.5 equiv) and 4% osmium tetroxide (0.136 g, 0.021 mmol, 0.1 equiv). The mixture was stirred at r.t. for 2 hours. Then it was diluted by EA, washed by water, dried over MgSO4, concentrated to load onto 12 g ISCO column and purified with 0-100% EtOAc[2% TEA]/Hexane to afford the product (0.14 g, 93%). 1H NMR (400 MHz, CDCl3) δ 11.23 (s, 1H), 8.28 (d, J=7.8 Hz, 1H), 8.07 (s, 1H), 7.92 (s, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.39 (d, J=1.5 Hz, 1H), 7.10 (d, J=9.3 Hz, 1H), 6.72-6.65 (m, 1H), 6.19-5.95 (m, 1H), 4.53-4.43 (m, 1H), 4.05-3.93 (m, 1H), 3.80-3.74 (m, 1H), 3.71 (s, 3H), 3.50 (d, J=16.1 Hz, 2H), 3.21-3.13 (m, 1H), 2.77 (s, 3H), 2.74-2.66 (m, 1H), 1.96 (d, J=13.6 Hz, 2H), 1.86-1.69 (m, 8H), 1.29 (s, 3H), 1.25 (s, 9H), 1.13 (d, J=6.0 Hz, 3H); LCMS (ESI, M+1): 704.25.
