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. Author manuscript; available in PMC: 2014 Aug 21.
Published in final edited form as: J Org Chem. 2004 Aug 6;69(16):5497–5500. doi: 10.1021/jo0493929

Scheme 2. Successful Synthesis of Saponin 1a.

Scheme 2

aReagents and conditions: (a) TMSOTf, CH2Cl2, 0 °C, 86% for 12; 84% for 8. (b) Ac2O, Pyr. (c) Diosgenin, NIS, TMSOTf, CH2Cl2, −42 °C, 63%. (d) Aqueous 80% AcOH, then aqueous 1 N NaOH, MeOH/CH2Cl2 2:1, 81%.