1: sodium tetrahydroborate; isopropyloxycarbonylchloride; triethylamine / tetrahydrofuran View Scheme

Kinetics; byproducts: CO; at 30-70 °C;

sodium hydroxide

Swern oxidation;

1.1: (R)-diphenylprolinol trimethylsilyl ether / ethanol / 48 h / 0 °C 2.1: sodium dihydrogenphosphate; sodium chlorite / 2-methyl-but-2-ene; water; tert-butyl alcohol / 1.5 h / 20 °C 3.1: thionyl chloride / dichloromethane / 6 h / 20 °C 3.2: 12 h / -25 °C 4.1: palladium 10 on activated carbon; hydrogen / ethanol / 13 h / 20 °C 5.1: sodium hydroxide / ethanol; water / 3 h / Reflux 5.2: 1 h / 160 °C / Inert atmosphere 6.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 0 - 20 °C 7.1: triethylamine / dichloromethane / 1 h / 20 °C 8.1: N,N-dimethyl-formamide / 1 h / 100 °C 9.1: hydrazine / ethanol / 3 h / Reflux 10.1: sodium hydroxide / tetrahydrofuran; water / 1 h / 20 °C View Scheme

in benzene at 35-50 °C,for 2-24 h; chromatography on Al2O3 with CH2Cl2/C6H14;

(i) NaH, DMF, (ii) /BRN= 2043439/, (iii) TsOH, I2, benzene; Multistep reaction;