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Reagents and conditions: (a) CH3OH, SOCl2, 0–23 °C (98%); (b) Boc2O, DMAP, CH2Cl2; (c) PdCl2(dppf), AcOK, DMF, 95 °C (74%); (d) F3CCO2H, 90 °C (97%); (e) H2, Rh/C, 100 psi (98%); (f) Pd(Ph3P)4, K2CO3, DME, 85 °C (71%); (g) (CF3CO)2O, NEt3, Et2O; (h) F3CCO2H, CH2Cl2 (70%); (i) (1) Ts-OH, NaNO2, H2O/acetonitrile, (2) NaN3, (83%); (j) CuSO4, sodium ascorbate (1 M aq); (k) KOH (1 M aq). R is defined in Tables 1 and 2.
