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. Author manuscript; available in PMC: 2013 Aug 13.
Published in final edited form as: J Med Chem. 2010 Sep 23;53(18):6730–6746. doi: 10.1021/jm100898v

Scheme 8a.

Scheme 8a

aReagents: (a) (Bu)2SnO, toluene, 110 °C then BzCl, 5 °C → room temperature; (b) TBDMSCl, imidazole, DMF, room temperature; (c) NaOMe, MeOH, room temperature; (d) Dess-Martin periodinane, CH2Cl2, room temperature; (e) Ph3PCH3Br or Ph3PCH2CH2CH3Br, n-BuLi, THF, −78 °C → room temperature; (f) Pd (10 wt% on carbon) or Pd(OH)2 (20 wt% on carbon), H2 (1 atm), EtOH, room temperature; (g) TFA or 36% aq. HCl in MeOH, room temperature; (h) Formaldehyde, 9-DAA, 1,4-dioxane, H2O, room temperature (for (3R,4S)-69) or 85 °C (for (3R,4S)-70).