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. Author manuscript; available in PMC: 2010 Nov 4.

Published in final edited form as: J Am Chem Soc. 2009 Nov 4;131(43):15909–15917. doi: 10.1021/ja906801g

Scheme 5 — bis-Silylation of Hydroxy Enone (−)-16^a

^a Reagents and conditions: a) TBSOTf (2.5 equiv), Et₃N (5.0 equiv), CH₂Cl₂, −78 → 0 °C, 1 h; b) TBSCl (1.5 equiv), Et₃N (4.0 equiv), 4-DMAP (0.1 equiv), CH₂Cl₂, 45 °C, 16 h; then TBSOTf (1.5 equiv), 0 °C, 4 h, 97%.