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. Author manuscript; available in PMC: 2013 Aug 9.
Published in final edited form as: J Med Chem. 2012 Jul 23;55(15):6751–6761. doi: 10.1021/jm3001218

Scheme 4.

Scheme 4

Reagents and conditions: (a) Ph3P=CH2Br, n-BuLi, THF, 85% (b) i) TFA, CH2CI2; ii) 2-methoxyacrylicacid, EDC, HOBt, DMF, 77% (c) Grubb's 2nd generation catalyst, CH2CI2, reflux, 65% (d) LiAIH4, THF, 70% (e) HCI, THF, reflux, 80% (f) NaBH4, MeOH, 19a:19b = 4:1,73% or L-selectride, THF, 0°C, 19a (80%), 19b (0%)