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. 2014 Jan 17;19(1):1120–1149. doi: 10.3390/molecules19011120

Scheme 4.

Preparation of the allyl bromides 18 and 22.

Scheme 4

Reagents and conditions: (a) 2,2-dimethoxypropane, APTS, acetone; (b) AcOH/H2O, 63%; (c) SOCl2, NEt3, CH2Cl2; (d) RuCl3, NaIO4, CH2Cl2/CH3CN, 85%; (e) NaN3, DMF, 92%; (f) AcOH/H2O; (g) Ac2O, DMAP, pyridine; (h) AcOH, H2SO4, Ac2O; (i) NaCN, DMF, 100%; (j) H2O2, NaOH, 100%; (k) HOCH2CH=CHCH2Br, BF3·OEt2, CH2Cl2, 78%.