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. Author manuscript; available in PMC: 2012 Feb 29.
Published in final edited form as: Angew Chem Int Ed Engl. 2007;46(43):8157–8159. doi: 10.1002/anie.200702537

Scheme 4.

Scheme 4

Reagents and conditions: a) PyBOP, iPr2NEt, CH3CN, 14 h, 28% (2 steps); b) Zn, HOAc, 12 h, 77%; c) 7, PyBOP, iPr2NEt, CH3CN, 1 h, 79%; d) Pd(PPh3)4, nBu3SnH, AcOH, CH2Cl2, 1 h, 74%; e) PyAOP, iPr2NEt, DMF, 12 h, 48%; f) LiOH, THF, 0 °C to rt, 75 min; g) Ac2O, pyr, 0 °C, 1.5 h then LiOH, THF, 15 min; h) TAS-F, DMF, 15 h, 17% (3 steps); PyAOP = (7-azabenzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate; PyBOP = (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate; TAS-F = tris(dimethylamino)sulfonium difluorotrimethylsilicate.