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. Author manuscript; available in PMC: 2010 Jun 10.
Published in final edited form as: J Am Chem Soc. 2009 Jun 10;131(22):7560–7561. doi: 10.1021/ja9029736

Scheme 3.

Scheme 3

Synthesis of propargyl ethers 13a

Reagents and conditions: (a) CeCl3, vinyl magnesium bromide, then HCl 1M, 65%; (b) (i) OsO4 (4 mol%), NMO (1.2 equiv.), acetone/t-BuOH/H2O; (ii) NaIO4, THF/H2O; (c) phenylacetylene, n-BuLi, THF; (d) KH, EtI, THF, 64% or KH, NaI, PMBCl, THF, 69% (over three steps).