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. Author manuscript; available in PMC: 2011 Apr 12.

Published in final edited form as: J Am Chem Soc. 2008 Aug 2;130(34):11297–11299. doi: 10.1021/ja804624u

Scheme 2 — ^a Reagents: (a) 2.5 mol % Grubbs’ second-generation catalyst, ethylene (300 psi), CH₂Cl₂, 25 °C (90%); (b) 50 mol % of EtAlCl₂, CH₂Cl₂, PhMe, 25 °C (74%, 1:1–1:3 cis:trans); (c) HONH₂ · HCl, MeOH, KOH, 25 °C (56%); (d) MoO₃, NaBH₄, MeOH, 25 °C (98%); (e) ClCO₂Me, Et₃N, CH₂Cl₂, 25 °C (56%); (f) (CH₂O)_n, TFA, CHCl₃, 25 °C (20%); (g) Na, NH₃, THF, −78 °C (98%); (h) LiAlH₄, THF, 25 °C (65%).