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. Author manuscript; available in PMC: 2011 Jan 1.
Published in final edited form as: J Org Chem. 2010 Jan 1;75(1):86–94. doi: 10.1021/jo901752v

Scheme 3.

Scheme 3

a) Lithium isopropylcyclohexylamine, THF, −78 °C, 3-(benzyloxy)propanoyl chloride; b) RuBr2(S)-binap, H2, MeOH, 60 psi, 60 °C, 96 hours; c) H2, 10% Pd/C, THF; d) TBSOTf, 2,6-lutidine, CH2Cl2; e) PhSO2Et, n-BuLi, −78 °C; f) Na(Hg), Na2HPO4, MeOH; g) LDA, −78 °C, ketone 11, −78 °C to −40 °C, aldehyde 7, 2 min.