Skip to main content
. Author manuscript; available in PMC: 2008 Jun 19.
Published in final edited form as: Org Biomol Chem. 2004 Mar 31;2(9):1315–1329. doi: 10.1039/b316502g

Scheme 6.

Scheme 6

Synthesis of the serine-based oxazoles. i. 2-Br–C6H4COCl (31), Et3N, CH2Cl2, 72%; ii. TBSCl or TIPSOTf, Et3N, DMAP, CH2Cl2, 70%; iii. LiAlH4, THF, 0 °C, 62–71%; iv. TsCl, DMAP, Et3N, CH2Cl2, 70–72%; v. t-BuLi, THF, −78 °C; Se powder, −78 to 0 °C then E–PhCH=CHCH2Br, 62–71%; vi. TBAF, HOAc, THF, 76–94%; vii. MeI, NaH, THF, 82%.