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. 2004 Jun 21;101(33):12030–12035. doi: 10.1073/pnas.0401932101

Scheme 1.

Scheme 1.

Reagents and conditions: reaction a, 1.0 eq of 19, 1.0 eq of 20, 6.5 eq of ZnCl2, POCl3,65°C, 3 h, 46% yield; reaction b, 3.3 eq of K2CO3, 5.1 eq of 21, 3.3 eq of KI, 10 mol % CuI, Me2CO, 45°C, 6 h, 25% yield; reaction c, 10% Pd/BaSO4, quinoline, EtOAc, 25°C, 6 h, 75% yield; reaction d, 25 eq of Ac2O, 25 eq of pyridine, 10 mol % N,N-dimethylaminopyridine, CH2Cl2, 35°C, 24 h, 85% yield; reaction e, 5.0 eq of Cs2CO3, 5.0 eq of MeI, DMF, 25°C, 15 min, 61% yield; reaction f, DMF, 120°C, 1 h, 49% yield of 1a, 35% yield of 22a;, 79% of 1b; 51% of 1c, 24% of 23c; and reaction g, 0.5 M K2CO3 (aq), MeOH, 25°C, 6 h, 91% yield. ND, not detected.