Scheme 4.
Reagents and conditions: a) 4, 2,4,6-C6H2Cl3COCl, Et3N, PhMe; then 15, DMAP, 23°C, 89%; b) TBAF, THF, 0°C, 66% (16: 12%); c) CCl3CN, DBU, CH2Cl2, 0°C, 73%; d) 3, BF3·OEt2, 4-Å molecular sieves, CH2Cl2, −78→23°C, 80%; e) TFA, H2O, 0°C; f) H2, Pd-C, MeOH, THF, 23°C, 64% (2 steps). DMAP = 4-dimethylaminopyridine, TFA = trifluoroacetic acid.