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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 1. Attempted Synthesis of Saponin 1a.

Scheme 1

aReagents and conditions: (a) FmocCl, Pyr, DMAP, 0 °C to room temperature, 87%. (b) Diosgenin, NIS, TMSOTf, CH2Cl2, −42 °C, 75%. (c) TMSOTf, CH2Cl2, 0 °C, 88% for 6; 27% for 8. (d) Et3N, 85% from 5.