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. Author manuscript; available in PMC: 2009 Jan 8.

Published in final edited form as: J Am Chem Soc. 2006 Sep 13;128(36):11906–11915. doi: 10.1021/ja062364i

Scheme 13a — ^a Reagents and conditions: (a) K₂CO₃, MeOH; (b) 67, 2,4,6-C₆H₂Cl₃COCl, Et₃N, PhMe; 85, DMAP (90%, 2 steps); (c) TBAF, THF (81%); (d) CCl₃CN, DBU, CH₂Cl₂ (56% α, plus 40% recovered 87); (e) NaOH, 1,4-dioxane; then Cs₂CO₃, H₂O, MeOH; (f) KHCO₃, BnBr, DMF (92%, 2 steps); (g) TESOTf, 2,6-lutidine, CH₂Cl₂; (h) HCO₂H, Pd(OAc)₂, Et₃N, PPh₃, 1,4-dioxane (81%, 2 steps); (i) BF₃·OEt₂, CH₂Cl₂ (70%); (j) TFA, H₂O, CH₂Cl₂, 0 °C; (k) 150 psi H₂, Pd/C, THF, MeOH (75%, 2 steps).