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Convergent synthesis of the pentafluorinated cryptophycin 31. Reagents and conditions: (a) Grubbs II catalyst, CH2Cl2, reflux, 16 h; (b) 19, DMAP, NEt3, 2,4,6-trichlorobenzoylchloride, THF, 0 °C, 1 h; (c) piperidine, DMF, rt, 16 h; (d) TFA, CH2Cl2, H2O, 0 °C, 3 h; (e) (CH3O)3CH, PPTS, CH2Cl2, rt, 2 h; (f) AcBr, CH2Cl2, rt, 4 h; (g) K2CO3, DME, ethylene glycol, rt, 3 min.
