Multi-step reaction with 14 steps
1.1: 90 percent / H2; AcOH / 10percent Pd/C / 20 °C / 2585.81 Torr
2.1: 92 percent / 1N NaOH / dioxane
3.1: 95 percent / (COCl)2; DMSO / CH2Cl2 / -78 °C
4.1: 40 percent / tetrahydrofuran
5.1: BH3*THF
5.2: 90 percent / H2O2; NaOH
6.1: 80 percent / CBr4; PPh3 / CH2Cl2
7.1: 90 percent / NaH / dimethylformamide
8.1: 95 percent / H2 / 10percent Pd/C / ethanol
9.1: 73 percent / DCC; DMAP / CH2Cl2 / 22 h / 0 - 20 °C
10.1: AcOH; H2O / tetrahydrofuran / 20 h / 20 °C
11.1: PCC / CH2Cl2 / 4 h
12.1: KMnO4 / acetone; H2O / 24 h
13.1: 100 percent / TFA / CH2Cl2 / 1 h / 20 °C
With
dmap; sodium hydroxide; potassium permanganate; borane-THF; oxalyl dichloride; carbon tetrabromide; water; hydrogen; sodium hydride; acetic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid;
10percent Pd/C;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
3.1: Swern oxidation / 4.1: Wittig reaction;
DOI:10.1021/ol010282n