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Reagents and conditions: a) DIBAL, CH2Cl2, −78 °C, 52%; b) NaBH4, ethanol, 0 °C to rt, 80%; c) Pd/C, H2, HCOOH, CH3OH, 20%; d) diethyl cyanomethylphosphonate, NaH, THF, 0 °C to rt; e) BCl3, CH2Cl2, −30 °C, 36% over two steps; f) methyl magnesium bromide, THF, 0 °C to 60 °C, 66%; g) BCl3, CH2Cl2, −30 °C, 46%; h) NaNO2, 80% AcOH, rt to 90 °C, 98%; i) BCl3, CH2Cl2, −30 °C, 48%.
