Omom Omom

Fig. 2.1.6. Synthesis of (Sa)-10 and (all-Sa)-11. (a) t-BuLi, THF, -78 °C, then ZnCl2, -78 °C to rt, 2 h; (b) 2-chloro-5-trimethylsilylethynyl-pyridine, Pd2dba3-CHCl3, t-Bu3P, THF, 83%; (c) KF, MeOH, 97%; (d) NaH, DMF, MOMCl, 80%; (e) n-BuLi, Et2O, rt, then I2, Et2O, -78 °C, 42% monoiodo and 40% diiodo compound;

(all-SJ-11

(f) Pd(OAc)2, t-Bu2(2-biph)P, Zn, DMF, rt, 62%; (g) KF, MeOH, rt, 79%; (h) Et3N, Cul, Pd2dba3-CHCl3, dppf, 50 °C, 77%; (i) conc. HCl, THF, MeOH, 95%; (j) Et3N, Cul, Pd2dba3-CHCl3, dppf, 50 °C, 96%; (k) conc. HCl, THF, MeOH, 97%.

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